Lithium Hydroxide → 1-{2-Chloro-5-[(S)-1-(4-chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethylamino]-benzyl}-3-methyl-azetidine-3-carboxylic acid

HRID 1629753Notes

Reaction equation

HRID 1629753 reaction equation
[ClH:1].C[O:3][C:4]([C:6]1([CH3:10])[CH2:9][NH:8][CH2:7]1)=[O:5].Cl.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C@H:19]([NH2:24])[C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=1[CH3:25].[Li+].[OH-]>>[Cl:1][C:13]1[CH:18]=[CH:17][C:16]([NH:24][C@@H:19]([C:16]2[CH:17]=[CH:18][C:13]([Cl:12])=[C:14]([CH3:25])[CH:15]=2)[C:20]([F:22])([F:23])[F:21])=[CH:15][C:14]=1[CH2:25][N:8]1[CH2:9][C:6]([CH3:10])([C:4]([OH:3])=[O:5])[CH2:7]1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 57517340(S)-1-(4-chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethylamine hydrochlorideHCID 67329141Methyl 3-methylazetidine-3-carboxylate hydrochloride

Product 1

HCID 533396561-{2-Chloro-5-[(S)-1-(4-chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethylamino]-benzyl}-3-methyl-azetidine-3-carboxylic acid

Procedure

The title compound was prepared according to Scheme 4 following a procedure analogous to Example 61 using 3-methyl-azetidine-3-carboxylic acid methyl ester hydrochloride (INT 14) in step 1 and (S)-1-(4-chloro-3-methyl-phenyl)-2,2,2-trifluoro-ethylamine hydrochloride in step 2, followed by a LiOH-mediated ester cleavage.

Sources & evidence

ORD record
ord-8c83f63bb9b54a9f8fa05ac593c23d00
Source dataset
uspto-grants-2014_07
Patent number
US08791100B2

Reaction notes

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