Ethyl 4-(4-nitro-3-phenyl-butyrylamino)benzoate → Ethyl 4-(3-naphthalen-2-yl-4-nitro-butyrylamino)benzoate

HRID 2422939Notes

Reaction equation

HRID 2422939 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([NH:15][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[O:14].[N+:27]([CH2:30]C(C1C=CC=CC=1)CC(NC1C=CC(C(OCC)=O)=CC=1)=O)([O-:29])=[O:28]>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH2:30][N+:27]([O-:29])=[O:28])[CH2:12][C:13]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1)=[O:14]

Participants

3

Reactant 2

HCID 67242330Ethyl 4-(4-nitro-3-phenyl-butyrylamino)benzoateHCID 67243223Ethyl 4-(3-naphthalen-2-yl-acryloylamino)benzoate

Product 1

HCID 67242987Ethyl 4-(3-naphthalen-2-yl-4-nitro-butyrylamino)benzoateYield 70%

Procedure

This was prepared from corresponding amide 42 (0.995 g, 2.88 mmol) in a similar manner as described for preparation of 47. Chromatography on silica gel performed using a FlashMaster 3 purification station (75:25 hexanes/ethyl acetate, Rf 0.20) afforded 48 (0.819 g, 2.017 mmol, 70%) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ 1.26 (3H, t, J 7.6 Hz), 2.85-2.93 (2H, m), 4.10 (1H, quint, J 8.0 Hz), 4.23 (1H, q, J 7.2 Hz), 5.02-5.10 (2H, m), 7.45-7.48 (2H, m), 7.54 (1H, dd, J 1.6, 8.8 Hz), 7.62 (2H, d, J 8.8 Hz), 7.82-7.87 (6H, m). 13C NMR (400 MHz, CDCl3) δ 14.52, 40.75, 40.79, 61.21, 79.48, 119.21, 124.97, 126.43, 126.65, 126.78, 126.87, 127.92, 128.04, 129.37, 130.94, 133.11, 133.59, 135.89, 141.68, 166.37, 168.54. MS (API-ES): m/z found 407 [M+H]+ (100%), HRMS (API-ES) m/z 407.1607 [M+H]+.

Workup

  1. customa FlashMaster 3 purification station (75:25 hexanes/ethyl acetate, Rf 0.20)

Sources & evidence

ORD record
ord-85dfe34f2b5c42b28c075bcf0a583e16
Source dataset
uspto-grants-2011_06
Patent number
US07960434B2

Reaction notes

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