Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoate → (4-{-2-{4-[Difluoro(phosphono)methyl]benzyl}-3-(4-fluorophenyl)-2-[4-(methoxycarbonyl)phenyl]-3-oxopropyl}phenoxy)-2,2-difluoroacetic acid

HRID 1371020Notes

Reaction equation

HRID 1371020 reaction equation
C([O:5][C:6](=[O:60])[C:7]([F:59])([F:58])[O:8][C:9]1[CH:57]=[CH:56][C:12]([CH2:13][C:14]([C:46]2[CH:55]=[CH:54][C:49]([C:50]([O:52][CH3:53])=[O:51])=[CH:48][CH:47]=2)([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([P:34]([O:41]C(C)(C)C)([O:36]C(C)(C)C)=[O:35])([F:33])[F:32])=[CH:27][CH:26]=2)[C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])=[CH:11][CH:10]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[F:33][C:31]([F:32])([P:34]([OH:36])([OH:41])=[O:35])[C:28]1[CH:29]=[CH:30][C:25]([CH2:24][C:14]([C:46]2[CH:55]=[CH:54][C:49]([C:50]([O:52][CH3:53])=[O:51])=[CH:48][CH:47]=2)([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[O:16])[CH2:13][C:12]2[CH:56]=[CH:57][C:9]([O:8][C:7]([F:59])([F:58])[C:6]([OH:60])=[O:5])=[CH:10][CH:11]=2)=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 18510258Methyl 4-[1-{4-[2-(tert-butoxy)-1,1-difluoro-2-oxoethoxy]benzyl}-1-{4-[[di(tert-butoxy)phosphoryl](difluoro)methyl]benzyl}-2-(4-fluorophenyl)-2-oxoethyl]benzoateHCID 21863450Trifluoroacetic acid methylene chloride

Product 1

HCID 10168904(4-{-2-{4-[Difluoro(phosphono)methyl]benzyl}-3-(4-fluorophenyl)-2-[4-(methoxycarbonyl)phenyl]-3-oxopropyl}phenoxy)-2,2-difluoroacetic acid

Procedure

The compound of Step 2 was treated with TFA/CH2Cl2 (1/1) at r.t. After a period of 18 h, the solvents were evaporated under reduced pressure to give the title compound (racemate).

Workup

  1. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-12bb4caca81f42748a04c45423d2cae2
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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