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

HRID 1881833ノート

反応式

HRID 1881833 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a8bc67dca34e4124a8dd7cafb95a7396
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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