Hydrochloric Acid → HCID 90289953、化合物

HRID 1471631ノート

反応式

HRID 1471631 の反応式
[C:1](=O)([S:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:14]([N:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)[CH3:17])=[O:15])[CH:7]=1)[CH3:2].[OH-].[K+].C([N:40]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:42]([CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=C1CBr)(=O)C.Cl>C(O)C>[C:30]([O:29][C:27]([NH:26][C@H:13]([C:14]([N:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[CH3:17])=[O:15])[CH2:12][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[CH2:5][CH2:4][S:3][CH2:1][C:2]1[NH:40][C:48]2[C:43]([C:42]=1[CH2:49][C:50]([O:52][CH2:53][CH3:54])=[O:51])=[CH:44][CH:45]=[CH:46][CH:47]=2)=[O:28])([CH3:31])([CH3:33])[CH3:32]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10860687HCID 10860687、化合物HCID 90327418HCID 90327418、化合物

生成物 1

HCID 90289953HCID 90289953、化合物収率 52.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (S)—S-3-(2-(tert-butoxycarbonylamino)-3-((4-methoxyphenyl)(methyl)amino)-3-oxopropyl)phenethyl ethanethioate (2.8 g, 5.74 mmol) in ethanol (20 ml) was added potassium hydroxide (0.64 g, 11.4 mmol). After 10 minutes, ethyl 2-(1-acetyl-2-(bromomethyl)-1H-indol-3-yl)acetate (2.2 g, 6.47 mmol) was added to the solution. The reaction was stirred for 2 hours at room temperature. The reaction was neutralized with 1N (aq) HCl and then extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (3-6% MeOH/DCM) to provide the desired product (2.0 g, 3.0 mmol), 52.3%. MS (m/z) 660 [M+H]+.

後処理

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe crude product was introduced to a silica gel loading column
  6. custompurified by column chromatography (3-6% MeOH/DCM)

出典と根拠

ORDレコード
ord-108dfab399ca454ca8805acf02c5e8f7
出典データセット
uspto-grants-2015_04
特許番号
US09012441B2

反応ノート

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