Trifluoroacetic acid → HCID 23405699, compound

HRID 489043Notes

Reaction equation

HRID 489043 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27]CC2C=CC(OC)=CC=2)=[O:26])[CH2:21][CH2:20]1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH:19]1[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=[O:26])[CH2:21][CH2:20]1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23387547HCID 23387547, compound

Product 1

HCID 23405699HCID 23405699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl 4-(N-benzyloxycarbonyl-L-valyloxy)-cyclohexanoate (12 g, 24.1 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred for 3 hours at room temperature. The solution was evaporated under reduced pressure and coevaporated two times with toluene. The residue was stirred 1 hour with about 100 ml ethanol and the white solid was filtered (byproduct). The solution was evaporated under reduced pressure and the product was isolated by silica gel column chromatography with toluene/acetone. Yield: 6.8 g=74%. The product can be activated and esterified directly to a drug or further modified as described below.

Workup

  1. customThe solution was evaporated under reduced pressure
  2. stirringThe residue was stirred 1 hour with about 100 ml ethanol
  3. filtrationthe white solid was filtered (byproduct)
  4. customThe solution was evaporated under reduced pressure
  5. customthe product was isolated by silica gel column chromatography with toluene/acetone

Sources & evidence

ORD record
ord-09d40ba1330641f78eec09f41f1d8575
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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