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

HRID 1757942Notes

Reaction equation

HRID 1757942 reaction equation
[CH3:1][C:2]([CH3:45])([CH3:44])[C:3](=[O:43])[O:4][CH2:5][O:6][P:7]([CH2:19][C:20]([N:22]1[CH:26]([C:27]([O:29]CC2C=CC=CC=2)=[O:28])[CH2:25][C:24]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:23]1)=[O:21])([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8].[H][H]>[Pd].CO>[CH3:1][C:2]([CH3:45])([CH3:44])[C:3](=[O:43])[O:4][CH2:5][O:6][P:7]([CH2:19][C:20]([N:22]1[CH:26]([C:27]([OH:29])=[O:28])[CH2:25][C:24]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[N:23]1)=[O:21])([CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:8]

Participants

5

Reactant 2

HCID 86738775(+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy](4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid, phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 20510338(+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy] (4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The diester product from part (d) (2.0 g.) is dissolved in 50 ml. of methanol containing 0.5 g. of 5% palladium on carbon catalyst and hydrogenated at 50 psi on a Parr apparatus until cessation of hydrogen uptake (2-4 hours). The catalyst is filtered off and the filtrate is concentrated in vacuo. The residue is triturated with acetonitrile or purified by flash chromatography to give (+)-4,5-dihydro-1-[[[(2,2-dimethyl-1-oxopropoxy)methoxy] (4-phenylbutyl)phosphinyl]acetyl]-3-phenyl-1H-pyrazole-5-carboxylic acid.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is triturated with acetonitrile
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-507bfdfd7d2d48c5b1c770bb4ddb094a
Source dataset
uspto-grants-1983_02
Patent number
US04371526

Reaction notes

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