Lithium Hydroxide → HCID 22958441, compound

HRID 1008565Notes

Reaction equation

HRID 1008565 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10](=[O:25])[C@@H:11]([NH:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12]([S:15][CH:16]([CH3:18])[CH3:17])([CH3:14])[CH3:13])=[O:4].[Li+].[OH-].OS([O-])(=O)=O.[K+].C(OCC)(=O)C>CO.O>[CH2:23]([O:22][C:20]([NH:19][C@@H:11]([C:12]([S:15][CH:16]([CH3:17])[CH3:18])([CH3:13])[CH3:14])[C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])=[O:25])=[O:21])[CH3:24]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 516920Potassium bisulfateHCID 54216343HCID 54216343, compound

Product 1

HCID 22958441HCID 22958441, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 1-[2-(R)-ethoxycarbonylamino-3-isopropylsulfanyl-3-methyl-butyryl-]-pyrrolidine-2-(S)-carboxylic acid methyl ester (0.45 g) and 0.06 g of LiOH in 6 mL of methanol and 1 mL of water was stirred for 16 h at ambient temperature. KHSO4 was added, the volatiles were pumped off followed by addition of water, extraction with ethyl acetate and concentration of the organic layer to give 0.34 g (79%) of the title compound as a colorless oil. (+)-APCI-MS: 361 (MH+).

Sources & evidence

ORD record
ord-ea443af35cf64e739a87d4fd59239372
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

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