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

HRID 1062569Notes

Reaction equation

HRID 1062569 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 co-evaporated 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-30ba7c749bee48e4b6771ba19d31f510
Source dataset
uspto-grants-2005_11
Patent number
US06962920B2

Reaction notes

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