| Identification | More | [Name]
N-Boc-trans-4-Hydroxy-L-proline methyl ester | [CAS]
74844-91-0 | [Synonyms]
(2R,4R)-4-HYDROXY-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER
(2S,4R)-1-(TERT-BUTOXYCARBONYL)-2-CARBOMETHOXY-4-HYDROXYPYRROLIDINE
(2S,4R)-BOC 4-HYDROXYPROLINE METHYL ESTER
BOC-HYDROXYPROLINE-OME
BOC-HYP-OME
BOC-L-4-HYDROXYPROLINE METHYL ESTER
BOC-L-4-TRANS-HYDROXYPROLINE METHYL ESTER
BOC-L-HYDROXYPROLINE METHYL ESTER
BOC-L-T-4-HYDROXYPROLINE METHYL ESTER
BOC-TRANS-4-HYDROXY-L-PROLINE METHYL ESTER
METHYL CIS-1-BOC-4-HYDROXY-D-PROLINATE
N-ALPHA-T-BUTOXYCARBONYL-L-HYDROXYPROLINE METHYL ESTER
N-BOC-4-HYDROXY-L-PROLINE METHYL ESTER
N-BOC-L-TRANS-4-HYDROXY-PROLINE METHYL ESTER
N-BOC-TRANS-4-HYDROXYL-L-PROLINE METHYL ESTER
N-BOC-TRANS-4-HYDROXY-L-PROLINE METHYL ESTER
N-T-BOC-TRANS-4-HYDROXY-L-PROLINE METHYL ESTER
N-(TERT-BUTOXYCARBONYL)-TRANS-HYDROXYL-L-PROLINE METHYL ESTER
N-BOC-TRANS-4-HYDROXY-L-PROLINE METHYL &
N-Boc-trans-hydro-L-prolinemethylester | [EINECS(EC#)]
616-143-2 | [Molecular Formula]
C11H19NO5 | [MDL Number]
MFCD00076981 | [Molecular Weight]
245.27 | [MOL File]
74844-91-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear Colourless Oil | [Melting point ]
92-96 °C (lit.) | [alpha ]
-65 º (c=1 CHCl3) | [Boiling point ]
132°C/0.05mmHg(lit.) | [density ]
1.216±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
Soluble in chloroform, dichloromethane and ethyl acetate. | [form ]
Crystalline Powder | [pka]
14.27±0.40(Predicted) | [color ]
White to light beige | [Optical Rotation]
[α]20/D -65°, c = 1% in chloroform | [Usage]
A potential iNOS inhibitor. | [InChI]
InChI=1S/C11H19NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h7-8,13H,5-6H2,1-4H3/t7-,8+/m1/s1 | [InChIKey]
MZMNEDXVUJLQAF-SFYZADRCSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C[C@H](O)C[C@H]1C(OC)=O | [LogP]
0.813 at 25℃ | [CAS DataBase Reference]
74844-91-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear Colourless Oil | [Uses]
(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic Acid 1-tert-Butyl Ester 2-Methyl Ester
roline scaffold. | [Uses]
A potential iNOS inhibitor. | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
The general procedure for the synthesis of N-Boc-trans-4-hydroxy-L-proline methyl ester from di-tert-butyl dicarbonate and trans-4-hydroxy-L-proline methyl ester hydrochloride was as follows: the trans-4-hydroxy-L-proline methyl ester hydrochloride (14.5 g, 0.1 mol) obtained in step I was suspended in CH2Cl2 (400 mL), cooled to 0 °C, and with stirring, sequentially Et3N (28 mL, 0.2 mol), DMAP (0.61 g, 5 mmol) and Boc anhydride (27.5 mL, 0.12 mol) were added. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure, ether was added to the residual solid, the solid was collected by filtration and washed well with ether. The filtrates were combined and concentrated under reduced pressure. The residue was dissolved in CH2Cl2, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl in turn, and the organic phase was dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give a light yellow oil, which was solidified by high vacuum treatment. The resulting solid was ground several times with hexane and dried in high vacuum to obtain 1-tert-butyl-2-methyl (2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate as a white solid (24.5 g, 100% yield). The product characterization data were as follows:(M+1) 245; 1H NMR (CDCl3, 300MHz) δ 4.54-4.37 (m, 2H), 3.75 (s, 3H), 3.70-3.40 (m, 2H), 2.48-2.21 (m, 2H), 2.13-2.0 (m, 1H), 1.46 (s, 3H), 1.41 (s, 6H). | [IC 50]
Non-cleavable Linker | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 22, p. 5699 - 5702
[2] Patent: WO2007/113634, 2007, A1. Location in patent: Page/Page column 60-61
[3] Tetrahedron Asymmetry, 2009, vol. 20, # 12, p. 1433 - 1436
[4] Journal of Chemical Research, 2009, # 11, p. 668 - 670
[5] Tetrahedron Letters, 2012, vol. 53, # 30, p. 3847 - 3849 |
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