Tert-butyl 4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)pyridin-2-yl)piperazine-1-carboxylate → (1R,2R)-2-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenylamino}-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid

HRID 557771Notes

Reaction equation

HRID 557771 reaction equation
C(OC(N1CCN(C2C=CC(NC(C3N=C(C4C=CC=CC=4)OC=3C(F)(F)F)=O)=CN=2)CC1)=O)(C)(C)C.[C:38]1([C:44]2[O:45][C:46]([C:74]([F:77])([F:76])[F:75])=[C:47]([C:49]([NH:51][C:52]3[CH:57]=[CH:56][C:55]([NH:58][C@H:59]4[CH2:63][CH2:62][N:61]([C:64]([CH:66]5[CH2:70][CH2:69][CH2:68][CH:67]5[C:71]([OH:73])=[O:72])=[O:65])[CH2:60]4)=[CH:54][CH:53]=3)=[O:50])[N:48]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[C:38]1([C:44]2[O:45][C:46]([C:74]([F:76])([F:75])[F:77])=[C:47]([C:49]([NH:51][C:52]3[CH:57]=[CH:56][C:55]([NH:58][C@H:59]4[CH2:63][CH2:62][N:61]([C:64]([C@@H:66]5[CH2:70][CH2:69][CH2:68][C@H:67]5[C:71]([OH:73])=[O:72])=[O:65])[CH2:60]4)=[CH:54][CH:53]=3)=[O:50])[N:48]=2)[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1

Participants

3

Reactant 2

HCID 52937267Tert-butyl 4-(5-(2-phenyl-5-(trifluoromethyl)oxazole-4-carboxamido)pyridin-2-yl)piperazine-1-carboxylateHCID 667382932-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenylamino}-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid

Product 1

HCID 57651921(1R,2R)-2-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenylamino}-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid

Procedure

With a method similar to that used for the preparation of 4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester above, 2-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenylamino}-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid was prepared as a mixture of diastereomers. The diastereomeric mixture was purified by chiral supercritical fluid chromatography (the first eluting peak) to yield (1R,2R)-2-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenylamino}-pyrrolidine-1-carbonyl)-cyclopentanecarboxylic acid as a yellow oil. HRMS calcd for C28H27F3N4O5 (M+H) 557.2007, obsd 557.2004

Workup

  1. customwas prepared as a mixture of diastereomers
  2. customThe diastereomeric mixture was purified by chiral supercritical fluid chromatography (the first eluting peak)

Sources & evidence

ORD record
ord-e36e6d72bfcc458eaac1f65ff19fe92e
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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