Triethylamine → N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide

HRID 275833Notes

Reaction equation

HRID 275833 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:13]=1[C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:23][NH:24][O:25][CH3:26].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>[Cl-]>[CH3:23][N:24]([O:25][CH3:26])[C:14](=[O:16])[C:13]1[CH:17]=[C:18]([OH:21])[CH:19]=[CH:20][C:12]=1[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183153542-(((Benzyloxy)carbonyl)amino)-5-hydroxybenzoic acid

Product 1

HCID 18315375N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide

Reagents, catalysts & solvents 1

HCID 312ChlorideSolvent

Procedure

2-Benzyloxycarbonylamino-5-hydroxybenzoic acid (6.0 g) and N,O-dimethylhydroxylamine hydrochloride (2.5 g) were dissolved in methylenb chloride (80 ml). To the solution were added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (4.6 g) and triethylamine (5 ml). The mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water, which was subjected to extraction with ethyl acetate (200 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give N-methyl-N-methyloxy-2-benzyloxycarbonylamino-5-hydroxybenzamide as a yellow oily product (5.0 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the concentrate was added water, which
  3. extractionwas subjected to extraction with ethyl acetate (200 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-5b2ab46e857a4748a4931ef6ff450c8c
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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