2-[(Benzoyloxy)methyl]benzoic acid → Benzamide, 3-methoxy-N,N-bis(1-methylethyl)-

HRID 376072Notes

Reaction equation

HRID 376072 reaction equation
NN=CC1C=CC(OCCCCCO[C:15]2[CH:29]=[CH:28][C:18]([C:19]([N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:17][C:16]=2[O:30][CH3:31])=CC=1.Cl.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(OCC1C=CC=CC=1C(O)=O)(=O)C1C=CC=CC=1>ClCCl>[CH3:31][O:30][C:16]1[CH:17]=[C:18]([CH:28]=[CH:29][CH:15]=1)[C:19]([N:21]([CH:25]([CH3:26])[CH3:27])[CH:22]([CH3:23])[CH3:24])=[O:20]

Participants

6

Reactant 4

HCID 940032-[(Benzoyloxy)methyl]benzoic acidHCID 1838004-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 4437433Benzamide, 3-methoxy-N,N-bis(1-methylethyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (3.0 g, 7.06 mmol) in 15 mL of dichloromethane is treated with 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride (1.67 g, 8.47 mmol), hydroxybenzotriazole (1.14 g, 8.47 mmol), and 2-(benzoyloxymethyl)benzoic acid (1.81 g, 7.06 mmol) and stirred at room temperature over 2 hours. The reaction is concentrated in vacuo and purified by chromatography on silica gel (50 g) with 60% ethyl acetate/hexane as the eluent to afford 4-[5-[4-amino[2-(benzoyloxymethyl)benzoyl]iminomethyl]phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide as a colorless foam:

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. custompurified by chromatography on silica gel (50 g) with 60% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-2791da59702d430a86a8d25915e66306
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

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