2-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl ester → HCID 67392027, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:5][C:6]1([CH3:11])[CH2:10][CH2:9][CH2:8][CH2:7]1>C(#N)C.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3](=[O:23])[C@H:4]([NH:12][C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:5][C:6]1([CH3:11])[CH2:7][CH2:8][CH2:9][CH2:10]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
2-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)-propionic acid methyl ester (7.6 g, 23.8 mmol) was dissolved in a mixture of acetonitrile (82 mL) and 0.2 M aqueous NaHCO3 (158 mL) and Alcalase 2.4 L (1.1 mL) was added and the reaction mixture wa stirred vigorously for 8 h. The reaction mixture was then evaporated at 30° C. to remove acetonitrile, and the aqueous residue was washed with ether. The ethereal layer was concentrated to yield 1.9 g of (R)-2-benzyloxycarbonylamino-3-(1-methylcyclopentyl)-propionic acid methyl ester. The aqueous phase was filtered with Celite, the pH was adjusted to 3 with 6 N HCl, and the solution was extracted with ethylacetate. The ethyl acetate layer was dried and evaporated to yield 1.4 g of (S)-2-benzyloxycarbonylamino-3-(1-methyl-cyclopentyl)-propionic acid. MS: 304.2 (M−1), 306.0 (M+1), 327.9 (M+Na).
Workup
- additionwas added
- customThe reaction mixture was then evaporated at 30° C.
- customto remove acetonitrile
- washthe aqueous residue was washed with ether
- concentrationThe ethereal layer was concentrated
Sources & evidence
- ORD record
- ord-a59b41dacc67462187e869d5848a8d2c
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07101880B2
Reaction notes
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