Sodium Carbonate → 2-(N-cyclohexyl-4-(3-formyl-4-nitrophenyl)oxybutyramidyl)acetamide

HRID 2308692Notes

Reaction equation

[CH:1]([C:3]1[CH:4]=[C:5]([O:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=[O:2].[CH:19]1([NH:25][C:26](=O)[CH2:27][NH2:28])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-:31].[Na+].[Na+]>O1CCCC1>[CH:19]1([N:25]([CH2:26][C:27]([NH2:28])=[O:31])[C:16](=[O:17])[CH2:15][CH2:14][CH2:13][O:12][C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([CH:1]=[O:2])[CH:4]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Conditions

Temperature: 5 °C

Procedure

A solution of 4-(3-formyl-4-nitrophenyl)oxybutyric acid chloride was added dropwise to a solution of N-cyclohexyl glycinamide (7.8 g) and sodium carbonate (6.90 g) in aqueous tetrahydrofuran cooled to 5° C. The reaction was stirred at room temperature for 1 hour, then extracted with ethyl acetate. The organic extract was washed with saturated sodium bicarbonate three times, 3×1M HCl and 2×brine, filtered and the solvent evaporated to give 2-(N-cyclohexyl-4-(3-formyl-4-nitrophenyl)oxybutyramidyl)acetamide as a solid, m.p. 104°-105° C. Similarly, treatment of cyclohexyl R7R8 -N-substituted acetamides from Preparation 2 gives the corresponding 2-(N-cyclohexyl-4-(3-nitro-4-formylphenyl)oxybutyramidyl-R7R8 -N-substituted acetamides.

Workup

extractionextracted with ethyl acetate
extractionThe organic extract
washwas washed with saturated sodium bicarbonate three times, 3×1M HCl and 2×brine
filtrationfiltered
customthe solvent evaporated

Sources & evidence

ORD record: ord-31b571cf72f14f3eb6170ebc5904f67f
Source dataset: uspto-grants-1987_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04690925

Reaction notes

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