Aniline → HCID 11298997, compound

HRID 2300020Notes

Reaction equation

HRID 2300020 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13](=[O:17])[CH:14](Br)[CH3:15])([CH3:11])([CH3:10])[CH3:9].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[C:8]([O:12][C:13](=[O:17])[C@H:14]([CH3:15])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 545327tert-Butyl 2-bromopropanoate

Product 1

HCID 11298997HCID 11298997, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of aniline (9.30 g, 0.10 mol), 2-bromopropionate t-butyl ester 20.9 g, 0.10 mol), Hunig's base (12.90 g, 0.10 mol) and toluene (200 mL) were stirred at reflux for 16 hours. The salt that formed was removed by filtration and the filtrate concentrated in vacuo to an oil (20 g). The oil was distilled. Pure N-phenylalanine t-butyl ester (18.0 g, 81% yield) was collected at 105-115 C (0.08 mm Hg).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe salt that formed
  3. customwas removed by filtration
  4. concentrationthe filtrate concentrated in vacuo to an oil (20 g)
  5. distillationThe oil was distilled

Sources & evidence

ORD record
ord-97a7aca0dd7541e0bf65d87db2151e25
Source dataset
uspto-grants-2002_12
Patent number
US06498004B1

Reaction notes

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