Sodium Bicarbonate → Cyclopropanesulphonic acid (17-hydroxy-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carbonyl)-amide

HRID 390118Notes

Reaction equation

HRID 390118 reaction equation
C(OC[O:5][CH:6]1[CH2:23][CH:22]2[CH:8]([C:9](=[O:35])[N:10]([CH3:34])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][CH:17]3[C:19]([C:25]([NH:27][S:28]([CH:31]4[CH2:33][CH2:32]4)(=[O:30])=[O:29])=[O:26])([NH:20][C:21]2=[O:24])[CH2:18]3)[CH2:7]1)C.C([O-])(O)=O.[Na+]>C1COCC1.CO.O.Cl>[OH:5][CH:6]1[CH2:23][CH:22]2[CH:8]([C:9](=[O:35])[N:10]([CH3:34])[CH2:11][CH2:12][CH2:13][CH2:14][CH:15]=[CH:16][CH:17]3[C:19]([C:25]([NH:27][S:28]([CH:31]4[CH2:32][CH2:33]4)(=[O:30])=[O:29])=[O:26])([NH:20][C:21]2=[O:24])[CH2:18]3)[CH2:7]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 72236618Cyclopropanesulfonic acid (17-ethoxymethoxy-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carbonyl)-amide

Product 1

HCID 72539645Cyclopropanesulphonic acid (17-hydroxy-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carbonyl)-amide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The ethoxy ether 1g was dissolved in a mixture of THF/MeOH/water (1:1:1, total volume 30 ml) whereafter 2.5 ml conc. hydrochloric acid was added while stirring. The reaction was stirred overnight at room temperature and was monitored by LC-MS. The reaction mixture was then poured into sat. aq. NaHCO3 (50 ml) and concentrated to half of the volume by rotary evaporation. The resulting mixture was acidified with 10% citric acid and extracted into DCM (3×20 ml). The combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated by rotary evaporation and dried at high vacuum overnight. The product was used without additional purification.

Workup

  1. additionwas added
  2. stirringThe reaction was stirred overnight at room temperature
  3. concentrationconcentrated to half of the volume by rotary evaporation
  4. extractionextracted into DCM (3×20 ml)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customdried at high vacuum overnight
  10. customThe product was used without additional purification

Sources & evidence

ORD record
ord-99318c265f3446809a73e123c51104ea
Source dataset
uspto-grants-2013_02
Patent number
US08383584B2

Reaction notes

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