Hydrochloric Acid → HCID 90289953, 화합물

HRID 1471631노트

반응식

HRID 1471631 반응식
[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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10860687HCID 10860687, 화합물HCID 90327418HCID 90327418, 화합물

생성물 1

HCID 90289953HCID 90289953, 화합물수율 52.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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]+.

후처리

  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)

출처 및 근거

ORD 기록
ord-108dfab399ca454ca8805acf02c5e8f7
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012441B2

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