p-Toluenesulfonic acid → Phenylmethyl N-[2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-1-oxo-3-phenylpropyl]-L-alaninate

HRID 1058762Notes

Reaction equation

HRID 1058762 reaction equation
[OH:1][P:2]([CH:16]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH2:4][CH:5]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6](O)=[O:7])=[O:3].[NH2:35][C@H:36]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH3:37].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[OH:3][P:2]([CH2:4][CH:5]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:6]([NH:35][C@H:36]([C:38]([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39])[CH3:37])=[O:7])([CH:16]([NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])[CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:1]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 726858benzyl (2S)-2-aminopropanoateHCID 186687012-Benzyl-3-[(1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl)(hydroxy)phosphoryl]propanoic acid

Product 1

HCID 15383287Phenylmethyl N-[2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-1-oxo-3-phenylpropyl]-L-alaninateYield 71.9%

Procedure

The process is performed according to the operating conditions described in 1.8, starting with 300 mg (0.62 mmol) of 3-[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]-2-(phenylmethyl)propanoic acid synthesized in 1.7., and 219 mg (0.62 mmol) of phenylmethyl alaninate in the form of the p-toluenesulphonic acid salt. 288 mg of product are recovered (yield=71.9%).

Workup

  1. customsynthesized in 1.7
  2. custom288 mg of product are recovered (yield=71.9%)

Sources & evidence

ORD record
ord-d5836d881db24acfade638a1ed066a04
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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