Trifluoroacetic acid → 5-(N-CBz-L-valyloxy)-2,2-dimethylvaleric acid

HRID 1170599Notes

Reaction equation

HRID 1170599 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:36])([CH3:35])[C:23]([O:25]CC1C=CC(OC)=CC=1)=[O:24])=[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>C(Cl)Cl>[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:19][CH2:20][CH2:21][C:22]([CH3:36])([CH3:35])[C:23]([OH:25])=[O:24])=[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 233875494-methoxybenzyl 5(N-CBz-L-valyloxy)-2,2-dimethylvalerate

Product 1

HCID 233875555-(N-CBz-L-valyloxy)-2,2-dimethylvaleric acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzyl 5-(N-CBz-L-valyloxy)-2,2-dimethylvalerate (8.24 g, 16.5 mmol) in CH2Cl2 (100 mL) at room temperature, was added trifluoroacetic acid (5 mL). After 1 h at room temperature, the reaction mixture was concentrated under reduced pressure. The crude product was column chromatographed (silica gel, 3→5% MeOH in CH2Cl2), to give 6.00 g of 5-(N-CBz-L-valyloxy)-2,2-dimethylvaleric acid. The compound can be activated and directly esterified to a drug or further modified as described below.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customchromatographed (silica gel, 3→5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-079d8ccee9ef4cb9b00178d23a9de931
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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