1-Hydroxybenzotriazole → Tert-butyl 4-{2-[methoxy(methyl)amino]-2-oxoethyl}benzoate

HRID 1881833Notes

Reaction equation

HRID 1881833 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].[C:6]([O:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:2][O:3][N:4]([CH3:5])[C:20](=[O:22])[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:11]([O:10][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:12])=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 598545182-(4-(Tert-butoxycarbonyl)phenyl)acetic acid

Product 1

HCID 59331582Tert-butyl 4-{2-[methoxy(methyl)amino]-2-oxoethyl}benzoateYield 80.4%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methoxymethanamine hydrochloride (5.00 g) in N,N-dimethylformamide (200 mL) was added triethylamine (7.1 mL), and the mixture was stirred at room temperature for 30 min. [4-(tert-Butoxycarbonyl)phenyl]acetic acid (10.0 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (12.2 g) and 1-hydroxybenzotriazole (8.60 g) were added to the reaction mixture under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (9.50 g, yield 80%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (3:2, volume ratio). MS: 280 (MH+).

Workup

  1. additionwere added to the reaction mixture under ice-
  2. temperaturecooling
  3. washwashed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a8bc67dca34e4124a8dd7cafb95a7396
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…