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1,2-Dichloroethane → 2,2-Dimethyl-propionic acid (R)-3-(4-methoxy-benzylsulfanyl)-2-[(7-nitro-1H-indole-2-carbonyl)-amino]-propyl ester

HRID 336463
ノート
印刷プレビュー

反応式

HRID 336463 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([OH:15])=O)=[CH:9]2)([O-:3])=[O:2].[NH2:16][C@@H:17]([CH2:26][S:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH2:28][S:27][CH2:26][C@H:17]([NH:16][C:13]([C:10]2[NH:11][C:12]3[C:8]([CH:9]=2)=[CH:7][CH:6]=[CH:5][C:4]=3[N+:1]([O-:3])=[O:2])=[O:15])[CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:34][CH:33]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 814097-nitro-1H-indole-2-carboxylic acidHCID 516892Sodium BicarbonateHCID 595430572,2-Dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester

生成物 1

HCID 59543073
2,2-Dimethyl-propionic acid (R)-3-(4-methoxy-benzylsulfanyl)-2-[(7-nitro-1H-indole-2-carbonyl)-amino]-propyl ester
収率 71.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

7-Nitro-1H-indole-2-carboxylic acid (8.2 g, 22.7 mmol) prepared in Step A and 2,2-dimethyl-propionic acid (R)-2-amino-3-(4-methoxy-benzylsulfanyl)-propyl ester (13.2 g, 27.2 mmol) prepared in Preparation 31 were dissolved in N,N-dimethylformamide (100 mL). EDC (6.6 g, 25.0 mmol) and HOBT (4.6 g, 25.0 mmol) were added thereto, and the mixture was stirred for 8 h at room temperature. Saturated aqueous sodium bicarbonate solution was added to the mixture to quench the reaction. The reaction mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure. The residue was purified by column chromatography to give the title compound (8.1 g, Yield 71%).

後処理

  1. customto quench
  2. customthe reaction
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationdistilled under reduced pressure
  7. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8ed55da7013a42d3b9e4db6d5d8fa378
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08889691B2

反応ノート

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