Trifluoroacetic acid → HCID 23387586, compound

HRID 488995Notes

Reaction equation

HRID 488995 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][C@@H:19]([CH3:32])[C:20]([O:22]CC1C=CC(OC)=CC=1)=[O:21])=[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@@H:19]([CH3:32])[C:20]([OH:22])=[O:21])=[O:17])[CH:13]([CH3:14])[CH3:15])([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 53733618HCID 53733618, compound

Product 1

HCID 23387586HCID 23387586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl (S)-(+)-2-(N-CBz-L-valyloxy)propionate (14.0 g, 31.5 mmole) in dichloromethane (50 ml) was added trifluoroacetic acid (25 ml) and the solution was stirred for five hours at room temperature. The solution was evaporated under reduced pressure and coevaporated two times with toluene. The product was isolated by silica gel column chromatography. Yield: 9.4 g=92%

Workup

  1. customThe solution was evaporated under reduced pressure
  2. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-dcb66e688fcc4829833c5403ec2842c7
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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