Lithium Hydroxide → HCID 66855209, compound

HRID 1970563Notes

Reaction equation

HRID 1970563 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:52])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:35]3[CH2:39][C:38]([F:41])([F:40])[C:37](=C=O)[C@@H:36]3OC)=[O:34])[N:28]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Li+].[OH-:54].C1[CH2:59][O:58]CC1>O>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([C:12](=[O:52])[C@@H:13]([NH:23][C:24]([C:26]2[CH:30]=[C:29]([O:31][CH2:32][C:33]([N:35]3[CH2:39][C:38]([F:40])([F:41])[CH2:37][C@H:36]3[C:59]([OH:58])=[O:54])=[O:34])[N:28]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[N:27]=2)=[O:25])[CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 866504804-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-4,4-difluoro-2-methoxy-carbonyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 66855209HCID 66855209, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 881 mg 4-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-4,4-difluoro-2-methoxy-carbonyl-pyrrolidin-1-yl)-2-oxo-ethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}-amino)-butyryl]-piperazine-1-carboxylic acid ethyl ester in 24 ml THF and 6 ml H2O were added 30 mg LiOH at 0° C. The reaction mixture was allowed to warm to RT and was then stirred for 3 h before being acidified by using Amberlite IR-120. The reaction mixture was filtered, washed with MeOH and the combined wash solutions concentrated to give the crude product which was used in the subsequent reaction. Yield: 711 mg.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed with MeOH
  3. concentrationthe combined wash solutions concentrated

Sources & evidence

ORD record
ord-febd2cef2b86471d939d3b86a76ca60e
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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