(+/-)-alpha-tert.Butyloxycarbonylamino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl) propanoic acid cinnamyl ester → (+/-)-alpha-Amino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl)propanoic acid cinnamyl ester

HRID 1109454Notes

Reaction equation

HRID 1109454 reaction equation
[CH2:1]([O:10][C:11](=[O:44])[CH:12]([NH:36]C(OC(C)(C)C)=O)[CH2:13][C:14]1[CH:15]=[C:16]([C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=2)[CH:17]=[C:18]([CH2:20][P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>FC(F)(F)C(O)=O>[CH2:1]([O:10][C:11](=[O:44])[CH:12]([NH2:36])[CH2:13][C:14]1[CH:15]=[C:16]([C:29]2[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=2)[CH:17]=[C:18]([CH2:20][P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[CH:19]=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

3

Reactant 1

HCID 56990101(+/-)-alpha-tert.Butyloxycarbonylamino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl) propanoic acid cinnamyl ester

Product 1

HCID 53895977(+/-)-alpha-Amino-3-(4'-chloro-5-(diethoxyphosphinyl)methyl-[1.1'-biphenyl]-3-yl)propanoic acid cinnamyl ester

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

5.5 g of the product of step c) and 50 ml aqueous trifluoroacetic acid (70%) are stirred at room temperature 20 hours. To the mixture are added CH2CL2 and dropwise aqueous KHCO3 solution. The organic phase is dried (Na2SO4) and evaporated. The residue is taken up in diethyl ether, filtered and evaporated to dryness, to give the heading compound as an oil.

Workup

  1. dry with materialThe organic phase is dried (Na2SO4)
  2. customevaporated
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bae87a276692495b90f5f30e6ac699be
Source dataset
uspto-grants-1994_06
Patent number
US05321016

Reaction notes

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