Trifluoroacetic acid → HCID 23387352, compound

HRID 990005Notes

Reaction equation

HRID 990005 reaction equation
COC1C=CC([CH2:7][C:8]([O:13][C:14](=[O:30])[C@H:15]([CH:27]([CH3:29])[CH3:28])[NH:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])(C)[C:9]([O-:11])=[O:10])=CC=1.FC(F)(F)C(O)=O>ClCCl>[C:17]([NH:16][C@H:15]([C:14]([O:13][CH:8]([CH3:7])[C:9]([OH:11])=[O:10])=[O:30])[CH:27]([CH3:28])[CH3:29])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866039364-methoxybenzyl-2-(N-CBZ-L-valyloxy)-propionate

Product 1

HCID 23387352HCID 23387352, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl-2-(N-CBZ-L-valyloxy)-propionate (7.8 g, 17.5 mmole) in dichloromethane (100 ml) was added trifluoroacetic acid (10 ml) and the solution was stirred for one hour at room temperature. The solution was evaporated under reduced pressure and the product was isolated by silica gel column chromatography. Yield: 5.0 g 1H-NMR (CDCl3) 0.94 (m, 6H) 1.56 (d, 3H) 2.30 (m, 1H) 4.42 (m, 1H) 5.12-5.30 (m, 4H) 7.28 (m, 5H)

Workup

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

Sources & evidence

ORD record
ord-7c263debc4db4379a9f9caae08cde616
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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