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

HRID 372972

Reaction equation

HRID 372972 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>C(Cl)Cl>[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 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 6344DichloromethaneSolvent

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-a7f824c3699a4447b3715861c05b289d
Source dataset
uspto-grants-1992_11
Patent number
US05162311

Linked notes

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