Sodium Bicarbonate → HCID 70231053, compound

HRID 1978035Notes

Reaction equation

HRID 1978035 reaction equation
CC([Si](C)(C)OC[CH:8]=[CH:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)(C)C.[CH3:33][OH:34].[OH2:35].[OH:36]OS([O-])=O.[K+].C([O-])(O)=O.[Na+]>O>[OH:34][CH2:33][CH:8]=[CH:9][S:10]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 22242641Methanol--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 70229768HCID 70229768, compound

Product 1

HCID 70231053HCID 70231053, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 0° C. suspension of Example 126C (1.34 g, 2.79 mmol) in a 2:1 mixture of methanol/ water (60 mL) was treated with oxone (4.28 g, 6.97 mmol) and NaHCO3 (0.58 g, 6.97 mmol), stirred at 0° C. for 1 hour, and then at room temperature for 18 hours. The suspension was diluted with water then extracted with ethyl acetate (3×30 mL). The combined extracts were washed with water, brine, dried, filtered, concentrated and purified on silica gel by flash column chromatography eluting with 1 to 2 hexanes/ethyl acetate to give 1.2 g of the desired product.

Workup

  1. waitat room temperature for 18 hours
  2. extractionthen extracted with ethyl acetate (3×30 mL)
  3. washThe combined extracts were washed with water, brine
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified on silica gel by flash column chromatography
  8. washeluting with 1 to 2 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-7273b022cf6d4406a51483dda178c224
Source dataset
uspto-grants-2001_05
Patent number
US06235786B1

Reaction notes

Loading…