Lithium Hydroxide → (S)-2-({5-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester

HRID 1970530Notes

Reaction equation

HRID 1970530 reaction equation
C[O:2][C:3](=[O:43])[C@@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:23][C:24]([N:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2[C:31](=[O:36])[NH:32][CH2:33][CH2:34][F:35])=[O:25])[N:19]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[N:18]=1)=[O:16])[CH2:5][CH2:6][C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[Li+].[OH-]>C1COCC1>[C:10]([O:9][C:7](=[O:8])[CH2:6][CH2:5][C@H:4]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:23][C:24]([N:26]2[CH2:30][CH2:29][CH2:28][C@H:27]2[C:31](=[O:36])[NH:32][CH2:33][CH2:34][F:35])=[O:25])[N:19]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[N:18]=1)=[O:16])[C:3]([OH:43])=[O:2])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86650478(S)-2-({5-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester 1-methyl ester

Product 1

HCID 86650477(S)-2-({5-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.30 g (S)-2-({5-[2-((S)-2-(2-Fluoro-ethylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-pentanedioic acid 5-tert-butyl ester 1-methyl ester in 9 ml THF were added 52 mg LiOH (as solution in 3 ml water). After 2 h the reaction mixture was neutralized with Amberlite IR-120, filtrated and washed with methanol.

Workup

  1. filtrationfiltrated
  2. washwashed with methanol

Sources & evidence

ORD record
ord-16eeb71852944bbe88a8e3faa9ed99d3
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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