4-Methylmorpholine → (2-{2-(3,5-Dimethylphenyl)-5-[1-(methoxymethylcarbamoyl)-1-methyl-ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert-butyl ester

HRID 1274400ノート

反応式

HRID 1274400 の反応式
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([CH3:25])([CH3:24])[C:21](O)=[O:22])[CH:18]=2)[NH:13][C:12]=1[C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[CH:27]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:35]1[C:39]2C=CC=CC=2N=N1.CN1CC[O:48][CH2:47]C1.CNOC.Cl.CN(C)CCCN=C=NCC>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([C:21](=[O:22])[NH:35][CH2:39][O:48][CH3:47])([CH3:25])[CH3:24])[CH:18]=2)[NH:13][C:12]=1[C:26]1[CH:27]=[C:28]([CH3:33])[CH:29]=[C:30]([CH3:32])[CH:31]=1)([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 5

HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 154585232-[3-(2-tert-butoxycarbonylaminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid

生成物 1

HCID 56977920(2-{2-(3,5-Dimethylphenyl)-5-[1-(methoxymethylcarbamoyl)-1-methyl-ethyl]-1H-indol-3-yl}ethyl)carbamic acid tert-butyl ester

実験手順

To a suspension of 2-[3-(2-tert-butoxycarbonylamino-ethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-2-methylpropionic acid (1.23 g in 15 mL N,N-dimethylformamide) at 0° C. was added 608 mg of 1-hydroxybenzotriazole (HOBt), 0.48 mL 4-methylmorpholine and 352 mg of N,O-dimethylhydroxylamine hydrochlorideand the mixture stirred at low temperature. After 15 minutes, 826 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) were added and the mixture warmed to room temperature. The reaction was quenched after 3.5 days by concentration in vacuo, resuspending in ethyl acetate and washing sequentially with water, 0.3N sodium bisulfate, water, saturated sodium bicarbonate and brine. The organic portion was dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (hexane:ethyl acetate, 3:1) to give the title compound (905 mg).

後処理

  1. customThe reaction was quenched after 3.5 days by concentration in vacuo
  2. washwashing sequentially with water, 0.3N sodium bisulfate, water, saturated sodium bicarbonate and brine
  3. dry with materialThe organic portion was dried over sodium sulfate
  4. customthe concentrate purified by flash chromatography on silica gel (hexane:ethyl acetate, 3:1)

出典と根拠

ORDレコード
ord-76dc6f2af19b40e597e06384e4569d6e
出典データセット
uspto-grants-2000_12
特許番号
US06156767

反応ノート

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