Triethylamine → HCID 18991668, compound

HRID 376071Notes

Reaction equation

HRID 376071 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:33]=[CH:32][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[O:21])=[C:18]([OH:31])[CH:17]=2)=[CH:7][CH:6]=1.[C:34](OC1C=CC=CC=1)(=[O:36])[CH3:35].C(N(CC)CC)C>C(Cl)Cl>[C:34]([N:2]=[N:3][CH2:4][C:5]1[CH:33]=[CH:32][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:27])[CH3:28])[CH:23]([CH3:25])[CH3:24])=[O:21])=[C:18]([OH:31])[CH:17]=2)=[CH:7][CH:6]=1)(=[O:36])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31229Phenyl acetateHCID 67744860HCID 67744860, compound

Product 1

HCID 18991668HCID 18991668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide monohydrochloride (220 mg, 0.46 mmol) in 10 mL anhydrous methylene chloride is treated with phenyl acetate (73 uL, 0.51 mmol) and triethylamine (73 uL, 0.51 mmol). The solution is stirred overnight, concentrated in vacuo and the resulting liquid is purified by chromatography on silica gel (15 g) with 80°-100% ethyl acetate/hexane as the eluent to afford 4-[5-[4-(acetyliminoaminomethyl)phenoxy]pentyloxy]-2-hydroxy-N,N-bis(1-methylethyl)benzamide as a colorless foam:

Workup

  1. concentrationconcentrated in vacuo
  2. customthe resulting liquid is purified by chromatography on silica gel (15 g) with 80°-100% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-0c3570441b1841e0a50aa6bed963a4f1
Source dataset
uspto-grants-1996_01
Patent number
US05488160

Reaction notes

Loading…