(S)-3-(Biphenyl-4-yl)-2-[(diphenylphosphonomethyl)-amino]-propionic acid benzyl ester → (S)-3-(biphenyl-4-yl)-2-[(diphenylphosphonomethyl)-amino]-propionic acid

HRID 1655293Notes

Reaction equation

HRID 1655293 reaction equation
C([O:8][C:9](=[O:42])[C@@H:10]([NH:24][CH2:25][P:26]([O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[C:15]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=[CH:13][C:12]([CH2:11][C@H:10]([NH:24][CH2:25][P:26]([O:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:27])[C:9]([OH:42])=[O:8])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 54430803(S)-3-(Biphenyl-4-yl)-2-[(diphenylphosphonomethyl)-amino]-propionic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 44285478(S)-3-(biphenyl-4-yl)-2-[(diphenylphosphonomethyl)-amino]-propionic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(S)-3-(Biphenyl-4-yl)-2-[(diphenylphosphonomethyl)-amino]-propionic acid benzyl ester (0.8 g, 1.38 mmol) is dissolved in ethyl acetate (25 mL) and treated with hydrogen (50 lbs) in a Parr apparatus in the presence of 10% palladium on carbon (0.8 g). After uptake of 1 mole, the catalyst is filtered off and the solvent is evaporated in vacuo. The solid residue is recrystallized at 0° from ethyl acetate/hexane. After being dried under high vacuum at 50°, (S)-3-(biphenyl-4-yl)-2-[(diphenylphosphonomethyl)-amino]-propionic acid is obtained as a white solid, m.p. 118°-119°; [α]405 =+9.49 (c 1.01, CHCl3).

Workup

  1. filtrationAfter uptake of 1 mole, the catalyst is filtered off
  2. customthe solvent is evaporated in vacuo
  3. customThe solid residue is recrystallized at 0° from ethyl acetate/hexane
  4. customAfter being dried under high vacuum at 50°

Sources & evidence

ORD record
ord-dcecc7d4dc9f42d5b64cfac901fbafb6
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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