Trifluoroacetic acid → HCID 23405699, compound

HRID 1790796Notes

Reaction equation

HRID 1790796 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-ea904dee533e4d0f807493821a2f3c37
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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