| Identification | More | [Name]
Z-ASP(OME)-OH | [CAS]
3160-47-2 | [Synonyms]
CBZ-ASP(OME)-OH
CBZ-L-ASPARTIC ACID 4-METHYL ESTER
N-ALPHA-CARBOBENZOXY-L-ASPARATIC ACID BETA-METHYL ESTER
N-BENZYLOXYCARBONYL-L-ASPARTIC ACID 4-METHYL ESTER
N-CBZ-L-ASPARTIC ACID BETA-METHYL ESTER
(S)-2-BENZYLOXYCARBONYLAMINO-SUCCINIC ACID 4-METHYL ESTER
(S)-2-N-CBZ-AMINO-SUCCINIC ACID 4-METHYL ESTER
Z-ASPARTIC ACID(OME)-OH
Z-ASP(OME)-OH
Z-L-ASPARTIC ACID 4-METHYL ESTER
Z-L-ASPARTIC ACID BETA-METHYL ESTER
N-cbz-L-aspartic acid B-methyl ester
CBZ-L-ASPARTIC ACID BETA METHYL ESTER
Z-L-ASPARTIC ACID B-METHYLESTER
N-carbobenzyloxy-L-aspartic acid beta-methyl ester
N-Cbz-L-aspartic acid β-methyl ester, Z-L-Aspartic acid 4-methyl ester | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C13H15NO6 | [MDL Number]
MFCD00133585 | [Molecular Weight]
281.26 | [MOL File]
3160-47-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
98 °C | [Boiling point ]
503.6±50.0 °C(Predicted) | [density ]
1.304±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
3.63±0.23(Predicted) | [color ]
White | [BRN ]
6279422 | [InChIKey]
PHMBNDDHIBIDRQ-JTQLQIEISA-N | [CAS DataBase Reference]
3160-47-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HS Code ]
29242990 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
peptide synthesis | [reaction suitability]
reaction type: solution phase peptide synthesis | [Synthesis]
30.5 g (207 mmol) (S)-2-Amino-4-methoxy-4-oxobutanoic acid was dissolved in 726 mL of distilled water and 260 mL of ether was added. Subsequently, 40.15 g (290 mmol) of potassium carbonate was added and stirred until completely dissolved, then 41.5 mL (290 mmol) of benzyl chloroformate was slowly added. The reaction mixture was stirred continuously for 4 hours at room temperature. After completion of the reaction, phase separation was carried out and the organic layer was discarded. The aqueous layer was washed several times with ether and the pH was subsequently adjusted with 1 N hydrochloric acid to 1. The aqueous layer was again extracted several times with ether, the organic layers were combined and dried over magnesium sulfate. Finally, 55 g of (2S)-4-methoxy-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid was obtained by vacuum concentration in 94% yield. The product was characterized by 1H NMR (300 MHz, CDCl3): δ 8.23 (s, 1H), 7.35 (m, 5H), 5.87 (d, 1H), 5.12 (s, 2H), 4.69 (m, 1H), 3.68 (s, 3H), 2.97 (dd, 2H). | [References]
[1] European Journal of Organic Chemistry, 2003, # 17, p. 3387 - 3397
[2] Patent: WO2012/148246, 2012, A2. Location in patent: Page/Page column 16
[3] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[4] Journal of Organic Chemistry, 2009, vol. 74, # 11, p. 4177 - 4187
[5] Tetrahedron Asymmetry, 2011, vol. 22, # 20-22, p. 1849 - 1854 |
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