Trifluoroacetic acid → HCID 54456052, compound

HRID 989981Notes

Reaction equation

HRID 989981 reaction equation
C(OC([NH:8][C:9]([CH3:30])([CH3:29])[CH2:10][O:11][C:12](=[O:28])[C@H:13]([CH:25]([CH3:27])[CH3:26])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]([CH3:30])([CH3:29])[CH2:10][O:11][C:12](=[O:28])[C@H:13]([CH:25]([CH3:26])[CH3:27])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57246576HCID 57246576, compound

Product 1

HCID 54456052HCID 54456052, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(N-(tert.-butyloxycarbonyl)-amino)-2-methyl-1-(N-benzyloxycarbonyl-L-valyloxy)-propane (10 g, 23 mmole) in dichloromethane (150 ml) was added trifluoroacetic acid (30 ml) and the mixture was stirred for 1 hour at room temperature. The solution was evaporated under reduced pressure and 10% sodium carbonate solution was added. The product was extracted four times with dichloromethane, dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with dichloromethane/methanol. Yield: 3.0 g=40% (crude)

Workup

  1. customThe solution was evaporated under reduced pressure and 10% sodium carbonate solution
  2. additionwas added
  3. extractionThe product was extracted four times with dichloromethane
  4. dry with materialdried with sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe product was isolated by silica gel column chromatography with dichloromethane/methanol

Sources & evidence

ORD record
ord-0181eace1d4245459f4130abcf430246
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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