Bromotrimethylsilane → (+)-4,5-dihydro-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, 1-(2,2-dimethyl-1-oxopropoxy)-2-ethoxy-2-oxoethyl ester

HRID 1757937Notes

Reaction equation

HRID 1757937 reaction equation
C([O:3][P:4]([CH2:16][C:17]([N:19]1[CH:23]([C:24]([O:26][CH:27]([O:33][C:34](=[O:39])[C:35]([CH3:38])([CH3:37])[CH3:36])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:25])[CH2:22][C:21]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])C.Br[Si](C)(C)C>ClCCl>[OH:5][P:4]([CH2:16][C:17]([N:19]1[CH:23]([C:24]([O:26][CH:27]([O:33][C:34](=[O:39])[C:35]([CH3:37])([CH3:38])[CH3:36])[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:25])[CH2:22][C:21]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[N:20]1)=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 57251309(+)-4,5-dihydro-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, 1-(2,2-dimethyl-1-oxopropoxy)-2-ethoxy-2-oxoethyl ester

Product 1

HCID 57190243(+)-4,5-dihydro-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, 1-(2,2-dimethyl-1-oxopropoxy)-2-ethoxy-2-oxoethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.0 g of the diester product from part (b) in 25 ml. of dry dichloromethane under argon is treated at ambient temperature with 0.6 g. of bromotrimethylsilane. After stirring overnight, the volatiles are removed in vacuo and the residue, dissolved in ethyl acetate, is washed with 5% sodium dihydrogen phosphate, water and saturated brine. The organic fraction is dried (MgSO4) and concentrated in vacuo. The residue is triturated with acetonitrile or purified by flash chromatography to give (+)-4,5-dihydro-1-[[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, 1-(2,2-dimethyl-1-oxopropoxy)-2-ethoxy-2-oxoethyl ester.

Workup

  1. customthe volatiles are removed in vacuo
  2. dissolutionthe residue, dissolved in ethyl acetate
  3. washis washed with 5% sodium dihydrogen phosphate, water and saturated brine
  4. dry with materialThe organic fraction is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is triturated with acetonitrile
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-94d92859dd0d4c0dbf340223e507c58b
Source dataset
uspto-grants-1983_02
Patent number
US04371526

Reaction notes

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