2-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl ester → HCID 67392027, compound

HRID 907599Notes

Reaction equation

HRID 907599 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]1

Participants

4

Reactant 1

HCID 673914702-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl ester

Product 1

HCID 67392027HCID 67392027, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 516892Sodium BicarbonateSolvent

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 was 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 (R)-2-benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl ester (1.9 g). The aqueous phase was filtered with Celite®, the pH was adjusted to 3 with 6N HCl, and the solution was extracted with ethylacetate. The ethyl acetate layer was dried and evaporated to yield 2(S)-benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid (1.4 g).

Workup

  1. additionwas added
  2. customThe reaction mixture was then evaporated at 30° C.
  3. customto remove acetonitrile
  4. washthe aqueous residue was washed with ether
  5. concentrationThe ethereal layer was concentrated

Sources & evidence

ORD record
ord-18bd46d095b847fb9fe9cfecf741c8df
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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