(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → HCID 86596347, compound

HRID 1272109Notes

Reaction equation

HRID 1272109 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:16][C:9]2=[N:10][C:11]([Cl:15])=[C:12]([CH3:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:23]([O:27][C:28]([N:30]1[CH2:34][C@H:33]([CH3:35])OS1(=O)=O)=[O:29])([CH3:26])([CH3:25])[CH3:24]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:16]([C@H:33]([CH3:35])[CH2:34][NH:30][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[C:9]2=[N:10][C:11]([Cl:15])=[C:12]([CH3:14])[CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 23665647Potassium tert-butoxideHCID 73013608HCID 73013608, compound

Product 1

HCID 86596347HCID 86596347, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 0.34 g (1.42 mmol) 6-chloro-5-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester in 7 mL N,N-dimethylformamide was cooled to 0° C. Potassium tert-butoxide (0.17 g, 1.50 mmol) was added and after 30 min. 0.37 g (1.57 mmol) (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester was added and the cooling bath was removed. After 3 h the reaction mixture was poured into 10% aqueous citric acid solution and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:5) as eluant to give the product as a colourless solid (87.8%).

Workup

  1. customthe cooling bath was removed
  2. additionAfter 3 h the reaction mixture was poured into 10% aqueous citric acid solution
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:5) as eluant

Sources & evidence

ORD record
ord-72d8bc8f1032483db0e3c07a6abde26f
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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