Trifluoroacetic acid → HCID 131719066, compound

HRID 1648387Notes

Reaction equation

HRID 1648387 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C@@H:9]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)C(C)C)(C)C.[CH2:43]([N:45]=[C:46]=[O:47])[CH3:44]>ClCCl>[CH2:43]([NH:45][C:46]([NH:8][C@@H:9]([C:17]([N:19]1[CH2:33][CH2:32][CH2:31][C@H:20]1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:47])[CH3:44]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 13391121HCID 13391121, compound

Product 1

HCID 131719066HCID 131719066, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of TFA.D-Phe-Pro-OBzl (10 g, 21.4 mmol) in dichloromethane (150 mL) was added N,N-diisopropylethylamine (3.73 mL, 21.4 mmol) followed by ethyl isocyanate (1.86 mL, 23.5 mmol). After stirring for 16 h, the solution was washed three times with 1N HCl, dried over Na2SO4, filtered and concentrated in vacuo to give 9.7 g (107%) of white foam.

Workup

  1. washthe solution was washed three times with 1N HCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f9576eae1ed945488d1b036812d6b120
Source dataset
uspto-grants-1995_07
Patent number
US05436229

Reaction notes

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