Acetonitrile → (+/-)-3-(4-{1-[3,5-Difluoro-4-(4-trifluoromethyl-pyrazol-1-yl)-phenoxy]-butyl}-benzoylamino)-propionic acid

HRID 537589Notes

Reaction equation

HRID 537589 reaction equation
C(O[C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:15][C:16]2[CH:21]=[C:20]([F:22])[C:19]([N:23]3[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[N:24]3)=[C:18]([F:32])[CH:17]=2)[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)C.[C:34]([OH:40])([C:36](F)(F)F)=[O:35].[C:41](#[N:43])C>>[F:22][C:20]1[CH:21]=[C:16]([CH:17]=[C:18]([F:32])[C:19]=1[N:23]1[CH:27]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:25]=[N:24]1)[O:15][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([C:4]([NH:43][CH2:41][CH2:36][C:34]([OH:40])=[O:35])=[O:33])=[CH:10][CH:9]=1)[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 6342Acetonitrile3×HCID 6422Trifluoroacetic acidHCID 68178668(+/-)-4-{1-[3,5-Difluoro-4-(4-trifluoromethyl-pyrazol-1-yl)-phenoxy]-butyl}-benzoic acid ethyl ester

Product 1

HCID 60152606(+/-)-3-(4-{1-[3,5-Difluoro-4-(4-trifluoromethyl-pyrazol-1-yl)-phenoxy]-butyl}-benzoylamino)-propionic acid

Procedure

The title compound was prepared by a method analogous to that described for Example 20 using (+/−)-4-{1-[3,5-difluoro-4-(4-trifluoromethyl-pyrazol-1-yl)-phenoxy]-butyl}benzoic acid ethyl ester. Column: Waters Atlantis d C18 4.6×50 mm, 5 μm; Modifier: TFA 0.05%; Gradient: 95% H20/5% acetonitrile linear to 5% H20/95% acetonitrile over 4.0 min, hold at 5% H20/95% acetonitrile to 5.0 min. Flow: 2.0 mL/min.; Retention time: 3.31 minutes. MS (M+1): 512.1.

Workup

  1. customto 5.0 min

Sources & evidence

ORD record
ord-00a4b0e94c0d4a3088ebf4d51e213664
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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