Toluene → Methyl 3-[4-(2-t-butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylate

HRID 1180804Notes

Reaction equation

C([C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:8])=[CH:5][CH:4]=1)=O.C1(P(=[CH:45][C:46]([O:48][CH3:49])=[O:47])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1(C)C=CC=CC=1>>[C:19]([O:18][C:17]([NH:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[NH:9][C:7]([C:6]1[CH:24]=[CH:25][C:3]([CH:50]=[CH:45][C:46]([O:48][CH3:49])=[O:47])=[CH:4][CH:5]=1)=[O:8])=[O:23])([CH3:20])([CH3:22])[CH3:21]

Participants

Reactant 3

HCID 1140Toluene

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

HCID 22668143Tert-butyl {2-[(4-formylbenzoyl)amino]phenyl}carbamate

Product 1

HCID 72479809Methyl 3-[4-(2-t-butoxycarbonylamino-phenylcarbamoyl)-phenyl]-acrylateYield 97%

Conditions

Temperature: 90 °C

Procedure

A stirred suspension of compound XI (500 mg, 1.47 mmol), methyl (triphenyl-phosphoranylidene)acetate (590 mg, 1.76 mmol) in anhydrous toluene (20 ml) was heated at 90° C. under nitrogen. After 2 days, the reaction mixture was concentrated and directly purified by flash chromatography on silica gel (AcOEt/hexane:30/70→40/60) to afford the title compound XII (568 mg, 1.43 mmol, 97% yield) as a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ(ppm): 9.32 (bs, 1H), AB system (δA=7.99, δB=7.62, J=8.4 Hz, 4H), 7.87 (d, J=7.9 Hz, 1H), 7.73 (s, J=15.8 Hz, 1H), 7.32–7.13 (m, 3H), 6.69 (bs, 1H), 6.53 (d, J=16.3 Hz, 1H), 3.83 (s, 3H), 1.53 (s, 9H).

Workup

concentrationthe reaction mixture was concentrated
customdirectly purified by flash chromatography on silica gel (AcOEt/hexane:30/70→40/60)

Sources & evidence

ORD record: ord-a2458136789343059e0a84cec83f13ee
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282608B2

Reaction notes

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