N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine → N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethy]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine

HRID 250298Notes

Reaction equation

HRID 250298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)=[O:16])[C@H:9]2[C:24]2[CH:39]=[CH:38][C:27]([O:28][CH2:29][C:30]([NH:32][C@@H:33]([C:35]([OH:37])=[O:36])[CH3:34])=[O:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[NH4+].O>CO.[BH4-].[Na+]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:11](=[O:12])[C@H:10]([S:13][CH2:14][CH:15]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[OH:16])[C@H:9]2[C:24]2[CH:39]=[CH:38][C:27]([O:28][CH2:29][C:30]([NH:32][C@@H:33]([C:35]([OH:37])=[O:36])[CH3:34])=[O:31])=[CH:26][CH:25]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 66843258N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanineHCID 86619100Ammonium acetate water

Product 1

HCID 66843176N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-hydroxyethy]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanineYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4311764Sodium borohydrideSolvent

Procedure

N-{[4-((2R,3R)-1-(4-fluorophenyl)-3-{[2-(4-fluorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}-D-alanine was dissolved in methanol (1.5 ml) whereafter sodium borohydride was added and the mixture was stirred for 30 minutes. After addition of ammonium acetate/H2O solution (2 ml), the methanol was evaporated and the product purified by preparative HPLC (CH3CN/0.1% ammoniumacetate 20:80-100:0). The fractions containing product confirmed by LC-MS were lyophilized and 27 mg (48%) of the desired product was obtained. m/z: 555.0 (M−1).

Workup

  1. additionwas added
  2. customthe methanol was evaporated
  3. customthe product purified by preparative HPLC (CH3CN/0.1% ammoniumacetate 20:80-100:0)
  4. additionThe fractions containing product

Sources & evidence

ORD record
ord-044f5e0883fd4a1fb3e16123d690e154
Source dataset
uspto-grants-2011_01
Patent number
US07863265B2

Reaction notes

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