Lithium Hydroxide → (S)-3-Hydroxy-2-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-propionic acid

HRID 411064Notes

Reaction equation

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

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 86656977(S)-3-Hydroxy-2-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-propionic acid ethyl ester

Product 1

HCID 86656978(S)-3-Hydroxy-2-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-propionic acidYield 80.3%

Procedure

(S)-3-Hydroxy-2-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-propionic acid (152 mg) was prepared by following General Procedure E starting from (S)-3-hydroxy-2-{[1-methyl-2-(6-trifluoromethoxy-benzothiazol-2-ylamino)-1H-benzoimidazole-5-carbonyl]-amino}-propionic acid ethyl ester (200 mg) and lithium hydroxide (64 mg).

Sources & evidence

ORD record: ord-7cdb4c0be1f54674acda3b34b6c59e93
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759535B2

Reaction notes

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