Hydrochloric Acid → HCID 68451882, compound

HRID 2355240Notes

Reaction equation

HRID 2355240 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.CC(C)([O-])C.[K+].[C:18]([O:22][C:23]([N:25]1[C:30]([CH3:32])([CH3:31])[CH2:29][CH2:28]OS1(=O)=O)=[O:24])([CH3:21])([CH3:20])[CH3:19].Cl>CN(C=O)C>[C:18]([O:22][C:23]([NH:25][C:30]([CH3:31])([CH3:32])[CH2:29][CH2:28][N:8]1[C:9]2[C:5](=[CH:4][C:3]([S:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 130195895-(Methylsulfanyl)-1H-indoleHCID 23665647Potassium tert-butoxideHCID 59383129HCID 59383129, compound

Product 1

HCID 68451882HCID 68451882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere 500 mg (2.6 mmol) 5-(methylsulphanyl)-indole (Yang et al., Heterocycles, 1992, vol. 34, No. 6, page 1169-1175) are dissolved in 6 ml DMF and combined with 357 mg (3.2 mmol) potassium-tert-butoxide with stirring and cooling with ice. Then the mixture is stirred for 10 minutes at 0° C. 768 mg (2.9 mmol) N-tert-butoxycarbonyl-4,4-dimethyl-[1,2,3]oxathiazinane-2,2-dioxide (Component XI) are added. The mixture is then stirred for three hours at ambient temperature. Then the reaction solution is poured onto water and hydrochloric acid (1.2 mmol) and extracted with ethyl acetate. The organic phases are combined, dried on sodium sulphate and freed from the solvent in vacuo.

Workup

  1. temperaturecooling with ice
  2. stirringThen the mixture is stirred for 10 minutes at 0° C
  3. stirringThe mixture is then stirred for three hours at ambient temperature
  4. extractionextracted with ethyl acetate
  5. customdried on sodium sulphate

Sources & evidence

ORD record
ord-3c0f46da622946f4be16837de259dbb8
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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