Potassium Carbonate → tert-Butyl 3-(4-(tert-Butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pent-4-ynoate

HRID 1427289노트

반응식

HRID 1427289 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)([CH:27]=O)[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:36]([O-])([O-])=O.[K+].[K+].[N+](=C(P(=O)(OC)OC)C(=O)C)=[N-]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]([C:29]1[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=1)([C:27]#[CH:36])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:7])([CH3:3])([CH3:2])[CH3:4]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 86705057tert-butyl 3-(4-(tert-butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)-4-oxobutanoateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

생성물 1

HCID 86705058tert-Butyl 3-(4-(tert-Butoxycarbonylamino)-1H-indol-1-yl)-3-(4-chlorophenyl)pent-4-ynoate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of the product of Step D (750 mg, 1.5 mmol) in MeOH (10 mL) was added K2CO3 (414 mg, 3 mmol) and dimethyl 1-diazo-2-oxopropylphosphonate (576 mg, 3 mmol). The mixture was stirred at room temperature for 2 h. After removing the organic solvent, the residue was added H2O (10 mL), extracted with ethyl acetate, and washed with brine (10 mL), dried over sodium sulfate, then filtered. The solvent was evaporated in vacuo, and the residue was purified by silica gel chromatography (EA/PE=1:8) to obtain the title compound as colorless solid. LC/MS m/z=495.2[M+H]+.

후처리

  1. customAfter removing the organic solvent
  2. additionthe residue was added H2O (10 mL)
  3. extractionextracted with ethyl acetate
  4. washwashed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by silica gel chromatography (EA/PE=1:8)

출처 및 근거

ORD 기록
ord-0e267e5764674bd4b2de006f63d14ba3
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933113B2

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