| Identification | More | [Name]
N-Boc-cis-4-Hydroxy-L-proline | [CAS]
87691-27-8 | [Synonyms]
(2S,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
BOC-(2S,4S)-(-)-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
BOC-CIS-4-HYDROXY-L-PROLINE
BOC-CIS-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
BOC-CISHYP-OH
N-ALPHA-BUTOXYCARBONYL-CIS-4-HYDROXY-L-PROLINE
N-BOC-CIS-4-HYDROXY-L-PROLINE
N-BOC-CIS-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID
N-T-BOC-CIS-4-HYDROXY-L-PROLINE
(S,S)-4-HYDROXY-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
(S,S)-CIS-1-N-BOC-4-HYDROXY-PROLINE
(2S,4S)-CIS-1-N-BOC-4-HYDROXY-PROLINE
(2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-HYDROXYPYRROLIDINE-2-CARBOXYLICACID
(2S,4S)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester | [EINECS(EC#)]
627-315-1 | [Molecular Formula]
C10H17NO5 | [MDL Number]
MFCD02094406 | [Molecular Weight]
231.25 | [MOL File]
87691-27-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
146 °C (D) (lit.) | [alpha ]
-50 º (c=0.67, MeOH) | [Boiling point ]
390.9±42.0 °C(Predicted) | [density ]
1.312±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Powder or Crystalline Powder | [pka]
3.80±0.40(Predicted) | [color ]
White to off-white | [Optical Rotation]
[α]20/D -50.0±3°, c = 0.67 in methanol | [InChI]
InChI=1S/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)/t6-,7-/m0/s1 | [InChIKey]
BENKAPCDIOILGV-BQBZGAKWSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)C[C@@H](O)C[C@H]1C(O)=O | [CAS DataBase Reference]
87691-27-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R50:Very Toxic to aquatic organisms. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
White powder | [Uses]
peptide synthesis | [reaction suitability]
reaction type: Boc solid-phase peptide synthesis | [Synthesis]
General procedure for the synthesis of N-Boc-cis-4-hydroxy-L-proline from (S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid: An appropriate amount of solvent was added to the reaction vessel and cooled to the specified temperature. Subsequently, the reducing agent (4.0~5.0 equivalents) was added in batches, taking care to control the rate of addition to avoid violent exotherm. The progress of the reaction was monitored by HPLC during the reaction. Upon completion of the reaction, the reaction solution was slowly poured into ice water to maintain the temperature at 0~5°C. The pH was adjusted to 0~5°C with dilute hydrochloric acid. The pH was adjusted to 2~3 with dilute hydrochloric acid and then extracted with ethyl acetate (EA) (5X each time, 3 times). All organic phases were combined, washed with saturated brine and dried with anhydrous sodium sulfate. The dried organic phase was concentrated under reduced pressure to give the crude product. Finally, the crude product was recrystallized in a mixed solvent of ethyl acetate and alkanes to give purified N-Boc-cis-4-hydroxy-L-proline. | [References]
[1] Patent: CN106543062, 2017, A. Location in patent: Paragraph 0021; 0024; 0027
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 7, p. 2253 - 2265
[3] Tetrahedron Letters, 1993, vol. 34, # 46, p. 7489 - 7492
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 251 - 259 |
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