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

HRID 1881833노트

반응식

HRID 1881833 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-a8bc67dca34e4124a8dd7cafb95a7396
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318746B2

반응 노트

불러오는 중…