Lithium Hydroxide → (1S,3R)-3-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid

HRID 557763Notes

Reaction equation

HRID 557763 reaction equation
C1(C2OC(C(F)(F)F)=C(C(NC3C=CC(N4CCN(C(C5CCCC5C(O)=O)=O)CC4)=CC=3)=O)N=2)C=CC=CC=1.[C:41]1([C:47]2[O:48][C:49]([C:78]([F:81])([F:80])[F:79])=[C:50]([C:52]([NH:54][C:55]3[CH:60]=[CH:59][C:58]([N:61]4[CH2:66][CH2:65][N:64]([C:67]([CH:69]5[CH2:74][CH2:73][CH2:72][CH:71]([C:75]([OH:77])=[O:76])[CH2:70]5)=[O:68])[CH2:63][CH2:62]4)=[CH:57][CH:56]=3)=[O:53])[N:51]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.COC(C1CCCC(C(N2CCN(C3C=CC(NC(C4N=C(C5C=CC=CC=5)OC=4C(F)(F)F)=O)=CC=3)CC2)=O)C1)=O.[OH-].[Li+]>>[C:41]1([C:47]2[O:48][C:49]([C:78]([F:79])([F:80])[F:81])=[C:50]([C:52]([NH:54][C:55]3[CH:60]=[CH:59][C:58]([N:61]4[CH2:66][CH2:65][N:64]([C:67]([C@@H:69]5[CH2:74][CH2:73][CH2:72][C@H:71]([C:75]([OH:77])=[O:76])[CH2:70]5)=[O:68])[CH2:63][CH2:62]4)=[CH:57][CH:56]=3)=[O:53])[N:51]=2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 4

HCID 3939Lithium HydroxideHCID 667382273-(4-{4-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid methyl esterHCID 66738247Rac-2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acidHCID 66738388Racemic 3-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid

Product 1

HCID 57651883(1S,3R)-3-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid

Procedure

With a method similar to that used for the preparation of rac-2-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclopentanecarboxylic acid above, racemic 3-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid was prepared from 3-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid methyl ester and lithium hydroxide. The crude racemate was purified by chiral supercritical fluid chromatography (second eluting peak) to yield (1S,3R)-3-(4-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenyl}-piperazine-1-carbonyl)-cyclohexanecarboxylic acid as an off-white solid. ES-MS calcd for C29H29F3N4O5 (m/e) 570.57, obsd 571.1 (M+H).

Workup

  1. customThe crude racemate was purified by chiral supercritical fluid chromatography (second eluting peak)

Sources & evidence

ORD record
ord-d78ef72f8db547f2b50d0017473e76ca
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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