Trifluoroacetic acid → HCID 23387520, compound

HRID 989969Notes

Reaction equation

HRID 989969 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([O:28]CC1C=CC(OC)=CC=1)=[O:27])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([NH:11][C@H:12]([C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26]([OH:28])=[O:27])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23387542HCID 23387542, compound

Product 1

HCID 23387520HCID 23387520, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzyl 2-(N-CBz-L-valyloxy)phenylacetate (4.25 g, 8.4 mmol), was dissolved in dichloromethane (40 ml). Triflouro acetic acid (8 ml) was added with cooling on ice. The mixture was allowed to reach room temperature and stirred for 40 min. The solvent was removed under reduced pressure and the crude product was recrystallized twice (hexan-ethyl acetate+a small amount of dichloromethane) to give the title compound (2.6 g, 80%). The compound can be activated and esterified to a drug or further modified as described below.

Workup

  1. temperaturewith cooling on ice
  2. customto reach room temperature
  3. customThe solvent was removed under reduced pressure
  4. customthe crude product was recrystallized twice (hexan-ethyl acetate+a small amount of dichloromethane)

Sources & evidence

ORD record
ord-405a4c565c0f4b8a959cad079be7ceb7
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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