5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester → 1-(2-tert-butoxycarbonylamino-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 506640ノート

反応式

HRID 506640 の反応式
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:29]([O:33][C:34]([N:36]1[CH2:40][CH2:39]OS1(=O)=O)=[O:35])([CH3:32])([CH3:31])[CH3:30]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:39][CH2:40][NH:36][C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:35])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][Si:16]([C:19]([CH3:21])([CH3:20])[CH3:22])([CH3:18])[CH3:17])=[CH:10][CH:9]=2)=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 226767305-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl esterHCID 235840203-Boc-1,2,3-oxathiazolidine 2,2-dioxideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 684656201-(2-tert-butoxycarbonylamino-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester収率 118.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The solution of 7.0 g (21.9 mmol) 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester in 60 mL N,N-dimethylformamide was cooled down to 0° C. and 2.7 g (24.1 mmol) potassium tert-butoxide was added. After 30 min., 5.4 g (24.2 mmol) 2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (prepared according to WO 02/072584) was added and the cooling bath was removed. After 1.5 hours, 10% aqueous ammonium chloride solution was added and the two-phase mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The thus obtained crude product (brown oil; 12.0 g, 100%) was used without further purification for the next step.

後処理

  1. customthe cooling bath was removed
  2. waitAfter 1.5 hours
  3. addition10% aqueous ammonium chloride solution was added
  4. extractionthe two-phase mixture was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-68759d4bbe334beca1b3775faf029930
出典データセット
uspto-grants-2010_08
特許番号
US07786109B2

反応ノート

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