Trifluoroacetic acid → 4-Methyl-4-(p-nitrobenzyloxycarbonyl)aminovaleric acid

HRID 1252222

Reaction equation

HRID 1252222 reaction equation
COC1C=CC(C[O:8][C:9](=[O:29])[CH2:10][CH2:11][C:12]([CH3:28])([NH:14][C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)=[O:16])[CH3:13])=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(OCC)C>[CH3:28][C:12]([NH:14][C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[O:16])([CH3:13])[CH2:11][CH2:10][C:9]([OH:29])=[O:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 539719334-Methyl-4-p-nitrobenzyloxycarbonylaminovaleric acid p-methoxybenzyl ester

Product 1

HCID 133343844-Methyl-4-(p-nitrobenzyloxycarbonyl)aminovaleric acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-methyl-4-p-nitrobenzyloxycarbonylaminovaleric acid p-methoxybenzyl ester (25 g), anisole (25 g) and trifluoroacetic acid (125 ml) was stirred for 15 minutes at room temperature. Evaporation of trifluoroacetic acid gave an oily residue which was then dissolved in diethyl ether. The ether solution was extracted with aqueous sodium carbonate. The aqueous layer was washed with diether ether, acidified with dilute hydrochloric acid and extracted with benzene. The benzene extract was washed with water, dried over anhydrous sodium sulfate and evaporated to give 4-methyl-4-p-nitrobenzyloxycarbonylaminovaleric acid.

Workup

  1. customEvaporation of trifluoroacetic acid
  2. customgave an oily residue which
  3. extractionThe ether solution was extracted with aqueous sodium carbonate
  4. washThe aqueous layer was washed with diether ether
  5. extractionextracted with benzene
  6. extractionThe benzene extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-ee09b96d6f97420b9c4ef0a3e6050de5
Source dataset
uspto-grants-1988_05
Patent number
US04742052

Linked notes

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