3-Phenylprop-2-enoyl chloride → {(4-Bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid, methyl ester

HRID 655177Notes

Reaction equation

HRID 655177 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[C:14](Cl)(=[O:23])[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[C:14](=[O:23])/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 660233-Phenylprop-2-enoyl chlorideHCID 974071methyl N-(4-bromophenyl)glycinate

Product 1

HCID 59212030{(4-Bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid, methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

(4-Bromophenylamino)acetic acid, methyl ester (8.74 g, 0.036 mol) was treated with cinnamoyl chloride (11.99 g, 0.072 mol) in pyridine (50 mL) in the presence of 4-dimethylaminopyridine (0.489 g, 0.004 mol). The reaction mixture was stirred at room temperature for 2 h. The crude product was purified by flash column chromatography on silica gel, eluting with ethyl acetate/dichloromethane (1:20), to give the title compound as a white crystalline solid (13.13 g, 98%). 1HNMR (300 MHz) (CDCl3) δ 3.67 (3H, s), 4.42 (2H, s), 6.28 (1H, d, J=16 Hz), 7.19 (2H, d), 7.2-7.3 (5H, m), 7.51 (2H, d) and 7.66 (1H, d, J=16 Hz).

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel
  2. washeluting with ethyl acetate/dichloromethane (1:20)

Sources & evidence

ORD record
ord-8bbd10e8897c4923bbc0341d5dbdbcd8
Source dataset
uspto-grants-2011_12
Patent number
US08071582B2

Reaction notes

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