Trifluoroacetic acid → HCID 513946, compound

HRID 987958Notes

Reaction equation

HRID 987958 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:22](=[O:45])[NH:23][CH2:24][CH2:25][CH2:26][C@H:27]([N:30]([S:35]([C:38]1[CH:43]=[CH:42][C:41]([NH2:44])=[CH:40][CH:39]=1)(=[O:37])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:28][OH:29])[CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@@H:8]([CH:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:22]([NH:23][CH2:24][CH2:25][CH2:26][C@H:27]([N:30]([S:35]([C:38]1[CH:39]=[CH:40][C:41]([NH2:44])=[CH:42][CH:43]=1)(=[O:37])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:28][OH:29])=[O:45]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 513938HCID 513938, compound

Product 1

HCID 513946HCID 513946, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.59 g of (1S,4S)-(1-{4-[(4-amino-benzenesulfonyl)-isobutyl-amino]-5-hydroxy-pentylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid tert-butyl ester in 5 mL of dichloromethane under stirring were added 5 mL of trifluoroacetic acid. The reaction was followed by TLC and upon disappearance of the starting material the mixture was evaporated in vacuo. The residue was taken up in ethyl acetate and the organic layer washed with aqueous 1.0N sodium hydroxide, with brine, dried over magnesium sulfate and filtered. The filtrate was evaporated and then placed under mechanical vacuum overnight to provide 0.49 g (94%) of title compound as a light brown foam. The product was used without further purification to give a series of diphenyl-propionamide derived tests compounds.

Workup

  1. customwas evaporated in vacuo
  2. washthe organic layer washed with aqueous 1.0N sodium hydroxide, with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated
  6. customplaced under mechanical vacuum overnight

Sources & evidence

ORD record
ord-6f6bfe7066494b4384cf03034780fa34
Source dataset
uspto-grants-2003_10
Patent number
US06632816B1

Reaction notes

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