4-Fluorobenzylamine → HCID 59641951, compound

HRID 2250478Notes

Reaction equation

HRID 2250478 reaction equation
[C:1]([NH:4][C@H:5]1[C:10](=[O:11])[O:9][C:7](=O)[CH2:6]1)(=[O:3])[CH3:2].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1>CC(C)=O>[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][N:18]2[C:7](=[O:9])[CH2:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C:10]2=[O:11])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 673264-FluorobenzylamineHCID 98050461HCID 98050461, compound

Product 1

HCID 59641951HCID 59641951, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

Following the method of Witiak et al. (J. Med. Chem., 1971, 14(1), 24-30), N-acetyl-D-aspartic acid anhydride (2.19 g, 13.9 mmol) and para-fluorobenzylamine (1.74 g, 13.9 mmol) in acetone (12 mL) were heated together in a sealed tube at 100° C. for 1 h. The solvent was then removed under reduced pressure. Acetic anhydride (15 mL) was added to the residue and the mixture heated 50 min. at 100° C. The solvent was removed under reduced pressure and the residue purified by flash column chromatography (silica, 10% methanol in dichloromethane) to give the product as a foam (3.16 g, 85%). HPLC retention time 1.94 min.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. additionAcetic anhydride (15 mL) was added to the residue
  3. temperaturethe mixture heated 50 min. at 100° C
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by flash column chromatography (silica, 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-50f2c55a4d5a48c883ea720f1808a8cb
Source dataset
uspto-grants-2008_01
Patent number
US07317032B2

Reaction notes

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