Triphenylphosphine → (2s)-2-{[3',5-Difluoro-4'-(phenylsulfonyl)biphenyl-2-yl]oxy}propanoic acid

HRID 1963666Notes

Reaction equation

HRID 1963666 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[F:15][C:16]1[CH:17]=[C:18]([C:31]2[C:32]([OH:38])=[CH:33][CH:34]=[C:35]([F:37])[CH:36]=2)[CH:19]=[CH:20][C:21]=1[S:22]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])=[O:23].[C:39]([O:44]C(C)(C)C)(=[O:43])[C@@H:40]([CH3:42])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[F:15][C:16]1[CH:17]=[C:18]([C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=2[O:38][C@@H:40]([CH3:42])[C:39]([OH:44])=[O:43])[CH:19]=[CH:20][C:21]=1[S:22]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10953655tert-butyl (2R)-2-hydroxypropanoateHCID 672389023',5-Difluoro-4'-(phenylsulfonyl)biphenyl-2-ol

Product 1

HCID 57572451(2s)-2-{[3',5-Difluoro-4'-(phenylsulfonyl)biphenyl-2-yl]oxy}propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (0.19 ml) was added to a solution of the product of example 2 part (iii) (250 mg), tert-butyl(R)-(+)-lactate (141 mg) and triphenylphosphine (252 mg) in tetrahydrofuran (10 ml) at 0° C. After 20 minutes the ice bath was removed and the reaction stirred at room temperature overnight. The reaction mixture was then adsorbed onto silica and purified using flash column chromatography (eluent 10% ethylacetate/hexane) to give the subtitle compound as an oil, yield 140 mg.

Workup

  1. customAfter 20 minutes the ice bath was removed
  2. custompurified

Sources & evidence

ORD record
ord-430b2e8b44a1496ca644e6e83aa79bd9
Source dataset
uspto-grants-2013_04
Patent number
US08415394B2

Reaction notes

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