Trifluoroacetic acid → Diethyl N-[4-(aminomethyl)benzoyl]-L-glutamate

HRID 2121451Notes

Reaction equation

HRID 2121451 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:10][C:11](=[O:38])[C@H:12]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[NH:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][NH:22]C(OC(C)(C)C)=O)=[CH:17][CH:16]=1)[CH3:9]>C(Cl)Cl>[NH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:14]([NH:13][C@H:12]([C:11]([O:10][CH2:8][CH3:9])=[O:38])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:30])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15292991Diethyl-N-[4-[[N-(tert-butyloxycarbonyl)amino]methyl]benzoyl]-L-glutamate

Product 1

HCID 10472190Diethyl N-[4-(aminomethyl)benzoyl]-L-glutamateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

About 1.8 ml trifluoroacetic acid was added dropwise to a stirred solution containing about 1.0 g of Compound 34 in about 20 ml CH2Cl2. The mixture was stirred at room temperature for 15 minutes, evaporated to dryness under reduced pressure, and coevaporated twice with about 30 ml absolute ethanol. The residue was then subjected to column chromatography on silica gel (1.5×15 cm), eluting with a gradient of 5-10% methanol in CHCl3 to yield about 0.68 g of Compound 35.

Workup

  1. customevaporated to dryness under reduced pressure
  2. washeluting with a gradient of 5-10% methanol in CHCl3

Sources & evidence

ORD record
ord-da2d63adcd90446caeb063cca5574866
Source dataset
uspto-grants-2004_02
Patent number
US06696455B1

Reaction notes

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