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 2105327Notes

Reaction equation

HRID 2105327 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-530054f56f964822a1cc88713fbe3a34
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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