Benzoic Acid → HCID 22467471, compound

HRID 1934733Notes

Reaction equation

HRID 1934733 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[CH2:5][NH:6][C:7](=[O:25])[C:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:9]=1[NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21](O)[CH2:20][CH2:19]1.C(O)(=O)C1C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:18]1([NH:17][C:9]2[CH:10]=[CH:11][C:12]([N+:14]([O-:16])=[O:15])=[CH:13][C:8]=2[C:7]([NH:6][CH2:5][C:4]2[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:2]([F:1])[CH:3]=2)=[O:25])[CH2:23][CH2:22][CH:21]=[CH:20][CH2:19]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178491160HCID 178491160, compound

Product 1

HCID 22467471HCID 22467471, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(3-fluoro-4-methoxybenzyl)-2-(trans-4-hydroxycyclohexylamino)-5-nitrobenzamide (262 mg), benzoic acid (115 mg) and diethyl azodicarboxylate (164 mg) in anhydrous tetrahydrofuran (6 mL) was added triphenylphosphine (247 mg). After stirring for one day at ambient temperature, the mixture was evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (4:1 to 2:1). Collection of an upper fraction gave 2-(3-cyclohexenylamino)-N-(3-fluoro-4-methoxybenzyl)-5-nitrobenzamide as yellow powders (40 mg).

Workup

  1. customthe mixture was evaporated in vacuo
  2. customThe residue was purified by a silica gel column chromatography
  3. washeluting with a mixture of hexane and ethyl acetate (4:1 to 2:1)
  4. customCollection of an upper fraction

Sources & evidence

ORD record
ord-c8f8b58539e34442a4365937fdcd1b1a
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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