Water → Benzyl 2-(2-fluoro-4-nitrobenzamido)acetate

HRID 1399440Notes

Reaction equation

[F-:1].[K+].[N+]([C:6]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9])([O-])=O.C1OCCOCCOCCOCCOCCOC1.O>CS(C)=O>[F:1][C:6]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:7]=1[C:8]([NH:10][CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9]

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of spray-dried KF (200 mg, 3.48 mmol), intermediate 1 (250 mg, 0.696 mmol) and catalytic amount of 18-crown-6 in dry DMSO (5 mL) was stirred at 140-150° C. for 30 min. After completion (TLC), the reaction mixture was poured into ice cooled water (100 mL) and stirred for 5 min. The solution was extracted with EtOAc (3×50 mL). The combined solution was dried over anhyd Na2SO4. The solution was filtered and evaporated the solvents. The residue was chromatographed over silica gel column using hexane:acetone (80:20) as eluents to give the product as a pale yellow color solid (106 mg, 46%), mp 104-106° C. 1H NMR (400 MHz, CDCl3): δ 8.30 (1H, t, J=8.0 Hz), 8.13 (1H, dd, J=8.6, 1.4 Hz), 8.04 (1H, dd, J=11.0, 1.8 Hz), 7.38 (5H, s), 5.25 (2H, s), 4.33 (2H, d, J=4.8 Hz); LC-MS (negative ion mode): m/z 331 (M−H)−.

Workup

additionAfter completion (TLC), the reaction mixture was poured into ice
stirringstirred for 5 min
extractionThe solution was extracted with EtOAc (3×50 mL)
dry with materialThe combined solution was dried over anhyd Na2SO4
filtrationThe solution was filtered
customevaporated the solvents
customThe residue was chromatographed over silica gel column

Sources & evidence

ORD record: ord-e49f2dd68c924514919791e2cd6dbd15
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906344B2

Reaction notes

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