Acetic Acid → HCID 53652779, compound

HRID 1417458Notes

Reaction equation

HRID 1417458 reaction equation
C(O)(=[O:3])C.[OH:5][C:6]1([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:7]1(SC)[S:19][CH3:20].C(=O)([O-])O.[Na+]>C1(C)C(C)=CC=CC=1>[CH3:20][S:19][C:7]1[C:8]2[NH:9][C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]=2[CH:17]=[CH:18][C:6]=1[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].[OH:5][C:6]1[CH:18]=[CH:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:7]=1[S:19][CH3:20].[OH:5][C:6]1([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:7]1=[O:3].[OH:5][C:6]12[CH2:23][C:24](=[O:26])[O:25][C:7]1([S:19][CH3:20])[C:8]1[NH:9][C:10]3[C:15]([C:16]=1[CH2:17][CH2:18]2)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 54493877HCID 54493877, compound

Product 4

HCID 53652779HCID 53652779, compoundHCID 53957871HCID 53957871, compoundHCID 54308108HCID 54308108, compoundHCID 54416390HCID 54416390, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.5 ml of glacial acetic acid was added to a solution of 3.37 g of tert-butyl (2-hydroxy-1,1-bismethylthio-1,2,3,4-tetrahydrocarbazol-2-yl)acetate, as obtained in Example 1, in 40 ml of xylene. The reaction mixture was subsequently refluxed for 1 hour and then neutralized by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The aqueous layer was extracted with ethyl acetate, and the organic extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 80 g of silica gel with a 19:1 v/v mixture of benzene and ethyl acetate as the eluent, to yield 2.40 g of the title compound, melting at 137°-138° C., 50 mg of 2-hydroxy-1-methylthiocarbazole (melting at 138°-140° C.), 85 mg of tert-butyl (2-hydroxy-1-oxo-1,2,3,4-tetrahydrocarbazol-2-yl)acetate (melting at 156°-157° C.) and 125 mg of 3,3a,4,5,10,10b-hexahydro-3a-hydroxy-10b-methylthiofuro[2,3-a]carbazol-2-one (obtained as an amorphous solid).

Workup

  1. temperatureThe reaction mixture was subsequently refluxed for 1 hour
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. additionwith a 19:1 v/v mixture of benzene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-24c545020aab421195631bee88377517
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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