Sodium Bicarbonate → HCID 68278815, compound

HRID 1506923Notes

Reaction equation

HRID 1506923 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([N:12]([C:21]1[S:25][C:24]2[CH2:26][CH2:27][CH2:28][CH2:29][C:23]=2[C:22]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])COCC[Si](C)(C)C)(=[O:11])=[O:10])[CH3:2].C(=O)([O-])O.[Na+]>Cl.CO>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([NH:12][C:21]1[S:25][C:24]2[CH2:26][CH2:27][CH2:28][CH2:29][C:23]=2[C:22]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=[O:10])=[O:11])[CH3:2]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68278723HCID 68278723, compound2×

Product 1

HCID 68278815HCID 68278815, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of ethyl 2-[N-(2-ethylbenzenesulphonyl)-N-(2-trimethylsilylethoxymethyl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (Intermediate 37, 0.107 g) in concentrated hydrochloric acid (1 ml) and methanol (3 ml) was heated at 80° C. for 1 hour. After cooling to room temperature, the mixture was added drop-wise to a mixture of ice and saturated aqueous sodium hydrogen carbonate solution (25 ml) and then extracted with ethyl acetate (3×15 ml). The combined organic layers were washed with brine (5 ml), dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-(2-ethylbenzenesulphonylamino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (0.041 g) as a white solid.

Workup

  1. additionthe mixture was added drop-wise
  2. extractionextracted with ethyl acetate (3×15 ml)
  3. washThe combined organic layers were washed with brine (5 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane (0-20%)

Sources & evidence

ORD record
ord-7ad1083f0f1e4f928903dc7464ececb7
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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