1-Hydroxybenzotriazole → Ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetate

HRID 1881929ノート

反応式

HRID 1881929 の反応式
[NH:1]([C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH2:2].[Si:10]([O:27][CH2:28][C:29](O)=[O:30])([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C.C(N(CC)CC)C>[Si:10]([O:27][CH2:28][C:29]([NH:2][NH:1][C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:30])([C:23]([CH3:25])([CH3:26])[CH3:24])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2786935Ethyl 2-hydrazinyl-2-oxoacetateHCID 111415642-((tert-Butyldiphenylsilyl)oxy)acetic acid

生成物 1

HCID 59331270Ethyl [2-({[tert-butyl(diphenyl)silyl]oxy}acetyl)hydrazino](oxo)acetate収率 30.3%

試薬・触媒・溶媒 3

HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of ethyl hydrazino(oxo)acetate (3.58 g) in acetonitrile (100 mL) were successively added triethylamine (6.86 mL), {[tert-butyl(diphenyl)silyl]oxy}acetic acid (7.74 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (5.20 g) and 1-hydroxybenzotriazole (415 mg) under ice-cooling. The reaction mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with water and saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (3.20 g, yield 30%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

後処理

  1. temperaturecooling
  2. washwashed with water and saturated aqueous sodium hydrogen carbonate
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-f81bd77762e7496785d175a139d9a3ec
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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