1,2-Dichloroethane → [2-(3,4-Dihydro-1H-isoquinolin-2-yl)-1-(1H-indol-3-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

HRID 2223246ノート

反応式

HRID 2223246 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][CH2:25][NH:24]1.OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.C(Cl)CCl>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]([CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][CH:12]=1)[C:20]([N:24]1[CH2:25][CH2:26][C:27]2[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23]1)=[O:22])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 70461,2,3,4-TetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 83169N-tert-Butoxycarbonyl-L-tryptophanHCID 178418300HCID 178418300、化合物

生成物 1

HCID 69900649[2-(3,4-Dihydro-1H-isoquinolin-2-yl)-1-(1H-indol-3-ylmethyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

tert-Butyloxycarbonyl-L-tryptophan (3.00 g, 9.9 mmol) and 1,2,3,4-tetrahydroisoquinoline (1.31 g, 9.9 mmol) were suspended in THF (20 ml). At a temperature of 0° C., hydroxybenzotriazole (1.33 g, 9.9 mmol), diisopropylethylamine (1.27 g, 9.9 mmol), and EDC (N-3-dimethylaminopropyl-N′-ethylcarbodiimide hydrochloride, 1.89 g, 9.9 mmol) were added. The reaction mixture was stirred overnight at r.t. The solvent was evaporated, the residue was taken up in ethyl acetate, washed with water, and dried (Na2SO4). After evaporation of the solvent, the title compound, MS: m/e=420.5 (M+H+), (2.90 g, 70%) was obtained by chromatographic purification of the residue (silica gel, MeOH, CH2Cl2).

後処理

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. customAfter evaporation of the solvent

出典と根拠

ORDレコード
ord-3b7b631a0825407d8466ed1fdd2dc211
出典データセット
uspto-grants-2008_05
特許番号
US07375099B2

反応ノート

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