Toluene → t-Butyl {2-[4-(3-oxo-propenyl)-benzoylamino]-phenyl}-carbamate

HRID 1180807Notes

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][CH:46]=[O:47])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:48]1(C)C=CC=CC=1>>[O:47]=[CH:46][CH:45]=[CH:48][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]([CH3:20])([CH3:21])[CH3:22])=[O:8])=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 1140Toluene

HCID 75051(Triphenylphosphoranylidene)acetaldehyde

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

Product 1

HCID 72479807t-Butyl {2-[4-(3-oxo-propenyl)-benzoylamino]-phenyl}-carbamateYield 86%

Conditions

Temperature: 80 °C

Procedure

A stirred suspension of compound XI (4.00 g, 11.75 mmol), (triphenylphosphoranylidene)-acetaldehyde (3.60 g, 11.83 mmol) in anhydrous toluene (100 ml) was heated at 80° C. under nitrogen. After 2 days, the reaction mixture was concentrated and directly purified by flash chromatography on silica gel (AcOEt/hexane:30/70) to afford the title compound XVI (3.70 g, 10.10 mmol, 86% yield) as a yellow sticky solid (slightly contaminated with the diene). 1H NMR (300 MHz, CDCl3) δ(ppm): 9.75 (d, J=7.8 Hz, 1H), 9.49 (bs, 1H), AB system (δA=8.03, δB=7.65, J=8.4 Hz, 4H), 7.85–7.72 (m, 1H), 7.52 (d, J=15.6 Hz, 1H), 7.33–7.05 (m, 3H), 7.05–6.90 (m, 1H), 6.78 (dd, J=15.6, 7.8 Hz, 1H), 1.53 (s, 9H).

Workup

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

Sources & evidence

ORD record: ord-11fad40011274fa78b968d2add116963
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07282608B2

Reaction notes

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