| Identification | More | [Name]
BOC-4-OXO-PRO-OME | [CAS]
102195-80-2 | [Synonyms]
BOC-4-OXO-L-PROLINE METHYL ESTER
BOC-4-OXO-PRO-OME
BOC-GAMMA-KETO-L-PROLINE METHYL ESTER
BOC-L-PRO(4-O)-OME
BOC-L-PRO(4-OXO)-OME
BOC-PRO-(4-KETO)-OME
N-T-BOC-4-OXO-L-PROLINE METHYL ESTER
(S)-N-ALPHA-TERT-BUTYLOXYCARBONYL-4-OXO-PROLINE METHYL ESTER
N-BOC-4-OXO-L-PROLINE METHYL ESTER
METHYL (2S)-N-BOC-4-OXOPYRROLIDINE-2-CARBOXYLATE
Boc-L-Pro(4-keto)-OMe
N-alpha-t-Butyloxycarbonyl-4-oxo-L-proline methyl ester
1-BOC-4-OXO-L-PROLINE METHYL ESTER
N-tert-butyloxycarbonyl-4-oxo-L-proline methyl ester
tert-Butyl (2S)-2-(methoxycarbonyl)-4-oxopyrrolidine-1-carboxylate, (2S)-4-Oxo-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid methyl ester, 1-tert-Butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate | [EINECS(EC#)]
625-165-1 | [Molecular Formula]
C11H17NO5 | [MDL Number]
MFCD01861778 | [Molecular Weight]
243.26 | [MOL File]
102195-80-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
35-40°C | [alpha ]
14 º (C=1 IN CHLOROFORM) | [Boiling point ]
333.1±42.0 °C(Predicted) | [density ]
1.209±0.06 g/cm3(Predicted) | [Fp ]
110 °C | [storage temp. ]
-20°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Powder | [pka]
-3.86±0.40(Predicted) | [Appearance]
Light yellow to brown Solid | [Optical Rotation]
[α]22/D +14.0°, c = 1 in chloroform | [InChI]
InChI=1S/C11H17NO5/c1-11(2,3)17-10(15)12-6-7(13)5-8(12)9(14)16-4/h8H,5-6H2,1-4H3/t8-/m0/s1 | [InChIKey]
UPBHYYJZVWZCOZ-QMMMGPOBSA-N | [SMILES]
N1(C(OC(C)(C)C)=O)CC(=O)C[C@H]1C(OC)=O | [CAS DataBase Reference]
102195-80-2(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 .
R41:Risk of serious damage to eyes. | [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 .
S39:Wear eye/face protection . | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
(2S)-1-Boc-4-oxo-proline Methyl Ester (cas# 102195-80-2) is a compound useful in organic synthesis. | [Synthesis]
General procedure for the synthesis of BOC-4-oxo-L-proline methyl ester from N-Boc-trans-4-hydroxy-L-proline methyl ester:
(a) To a solution of methyl (2S,4R)-1-Boc-4-hydroxypyrrolidine-2-carboxylate (40 g, 157 mmol) in dichloromethane (DCM, 500 mL) was added Days-Martin oxidizer (DMP, 80 g, 189 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 4 h. Upon completion of the reaction, the reaction was quenched with sodium bisulfite (NaHSO3) solution. The reaction mixture was extracted with dichloromethane (DCM) and the organic phase was washed with aqueous sodium bicarbonate (NaHCO3) solution. Concentration of the organic phase afforded the title intermediate (2S)-1-tert-butoxycarbonyl-4-oxopyrrolidine-2-carboxylic acid methyl ester (33 g, 89% yield) as a colorless oil.
1H NMR (400 MHz, CDCl3): δ (ppm) 1.51 (s, 9H), 2.550-2.597 (d, 1H, J = 18.8Hz), 2.876-2.944 (t, 1H, J = 13.6Hz), 3.895 (s, 3H), 3.766-3.895 (m, 1H), 4.696- 4.814 (m, 1H). | [References]
[1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 5, p. 740 - 742
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1557 - 1572
[3] Journal of the American Chemical Society, 2016, vol. 138, # 7, p. 2443 - 2453
[4] Angewandte Chemie - International Edition, 2002, vol. 41, # 9, p. 1600 - 1602
[5] Tetrahedron Letters, 2003, vol. 44, # 42, p. 7809 - 7812 |
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