Ethyl 7-bromo-1H-indole-2-carboxylate → (r)-7-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-1h-indole-2-carboxylic acid ethyl ester

HRID 1760599노트

반응식

HRID 1760599 반응식
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Br:15])=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([CH3:34])OS1(=O)=O)=[O:28])([CH3:25])([CH3:24])[CH3:23]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([C@H:32]([CH3:34])[CH2:33][NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[Br:15])=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 7017885Ethyl 7-bromo-1H-indole-2-carboxylateHCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 68887802(r)-7-Bromo-1-(2-tert-butoxycarbonylamino-1-methyl-ethyl)-1h-indole-2-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 8.1 g (30.1 mmol) 7-bromo-1H-indole-2-carboxylic acid ethyl ester in 120 ml N,N-dimethylformamide was cooled to 0° C. and 3.55 g (31.6 mmol) potassium tert-butoxide was added. After 30 min., 7.86 g (33.1 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester were added and the cooling bath was removed. After 20 h the reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and evaporated. The resulting yellow oil was chromatographed on silica gel (0.032-0.063 mm) with tert-butyl methyl ether: n-hexane (1:8) as eluant to give the desired compound as a yellow oil. ISP-MS: m/e=427.3 ([M+H+]).

후처리

  1. customthe cooling bath was removed
  2. additionAfter 20 h the reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting yellow oil was chromatographed on silica gel (0.032-0.063 mm) with tert-butyl methyl ether: n-hexane (1:8) as eluant

출처 및 근거

ORD 기록
ord-1486662615d64122a6df75de1cc7a961
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844345B2

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