Lithium Hydroxide → (2S,4R)-2-(5-Carboxy-3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1527362Notes

Reaction equation

HRID 1527362 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([F:13])[CH2:10][C@H:9]1[C:14](=[O:29])[NH:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([O:25]C)=[O:24])[CH:20]=[C:19]([Cl:27])[C:18]=1[F:28])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([F:13])[CH2:10][C@H:9]1[C:14](=[O:29])[NH:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([OH:25])=[O:24])[CH:20]=[C:19]([Cl:27])[C:18]=1[F:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68283553(2S,4R)-2-(3-Chloro-2-fluoro-5-methoxycarbonyl-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68283054(2S,4R)-2-(5-Carboxy-3-chloro-2-fluoro-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a mixture of (2S,4R)-2-(3-chloro-2-fluoro-5-methoxycarbonyl-benzylcarbamoyl)-4-fluoro-pyrrolidine-1-carboxylic acid tert-butyl ester (140 mg, 0.3 mmol) in THF/MeOH/H2O 2:1:1 (4 mL) was added LiOH (7 mg, 0.3 mmol). The reaction mixture was stirred for 4 h at ambient temperature and the solvent was removed in vacuo to give the title compound which was used without further purification. MS (LC/MS): 319.0 [M−100]+. tR (HPLC conditions c): 4.40 min.

Workup

  1. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5cb023e8f8f64d2e94b9f5dbdae63c2d
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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