Lithium Hydroxide → (3S)-8-[2-amino-6-[(1R)-1-[4-chloro-2-(3-sulfamoylphenyl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-3-carboxylic acid

HRID 1499195Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:22][CH2:21][C:11]3([CH2:15][NH:14][C@H:13]([C:16]([O:18]CC)=[O:17])[CH2:12]3)[CH2:10][CH2:9]2)[CH:5]=[C:4]([O:23][C@H:24]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([S:42](=[O:45])(=[O:44])[NH2:43])[CH:37]=2)[C:25]([F:28])([F:27])[F:26])[N:3]=1.[Li+].[OH-]>>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:9][CH2:10][C:11]3([CH2:15][NH:14][C@H:13]([C:16]([OH:18])=[O:17])[CH2:12]3)[CH2:21][CH2:22]2)[CH:5]=[C:4]([O:23][C@H:24]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][C:30]=2[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([S:42](=[O:44])(=[O:45])[NH2:43])[CH:37]=2)[C:25]([F:28])([F:27])[F:26])[N:3]=1

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 131734249(S)-ethyl 8-(2-amino-6-((R)-1-(5-chloro-3'-sulfamoyl-[1,1'-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate

Product 1

HCID 117952268(3S)-8-[2-amino-6-[(1R)-1-[4-chloro-2-(3-sulfamoylphenyl)phenyl]-2,2,2-trifluoroethoxy]pyrimidin-4-yl]-2,8-diazaspiro[4.5]decane-3-carboxylic acid

Procedure

Hydrolysis of (S)-ethyl 8-(2-amino-6-((R)-1-(5-chloro-3′-sulfamoyl-[1,1′-biphenyl]-2-yl)-2,2,2-trifluoroethoxy)pyrimidin-4-yl)-2,8-diazaspiro[4.5]decane-3-carboxylate using the LiOH general method provided the title compound as an off-white solid.

Sources & evidence

ORD record: ord-e45bcc1206e343a7b066f3d17e876afd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199994B2

Reaction notes

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