Trifluoroacetic acid → HCID 53966558, compound

HRID 1790777Notes

Reaction equation

HRID 1790777 reaction equation
COC1C=CC(C[C:8]2[C:16]([O:17][C:18](=[O:34])[C@H:19]([CH:31]([CH3:33])[CH3:32])[NH:20][C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])=[CH:15][CH:14]=[CH:13][C:9]=2[C:10]([O-:12])=[O:11])=CC=1.FC(F)(F)C(O)=O>ClCCl>[CH2:24]([O:23][C:21]([NH:20][C@H:19]([C:18]([O:17][C:16]1[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11])=[O:34])[CH:31]([CH3:33])[CH3:32])=[O:22])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86585844HCID 86585844, compound

Product 1

HCID 53966558HCID 53966558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl-3-(N-benzyloxycarbonyl-L-valyloxy)-benzoate (13.7 g, 27.8 mmole) in dichloromethane (150 ml) was added trifluoroacetic acid (20 ml) and the mixture was stirred for 2 hours at room temperature. The solution was evaporated under reduced pressure and the product crystallized from toluene. Yield: 10.1 g=87%. The compound can be activated and esterified to a drug or further modified as described below

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customthe product crystallized from toluene

Sources & evidence

ORD record
ord-bdcc6a57c94444a9bf5ef696bb0a5468
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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