Sodium Bicarbonate → HCID 69882460, compound

HRID 2120350Notes

Reaction equation

HRID 2120350 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:24])[N:21]([CH3:23])[CH3:22])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:5]=[CH:4][C:3]=1[NH:25][C:26](=[O:34])[C@:27]([OH:33])([CH3:32])[C:28]([F:31])([F:30])[F:29].C([O-])(O)=O.[Na+]>Cl.O.CCO.[Fe]>[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20](=[O:24])[N:21]([CH3:23])[CH3:22])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[CH:5]=[CH:4][C:3]=1[NH:25][C:26](=[O:34])[C@:27]([OH:33])([CH3:32])[C:28]([F:30])([F:31])[F:29]

Participants

7

Reactant 2

HCID 516892Sodium BicarbonateHCID 69824886HCID 69824886, compound

Product 1

HCID 69882460HCID 69882460, compoundYield 86.9%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Iron (324 mg) and conc. hydrochloric acid (1 drop) was added to a suspension of (R)-N-{2-chloro-3-nitro-4-[4-(N,N-dimethylcarbamoyl)phenyl]sulphonylphenyl}-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 63) (305 mg) in water (0.25 ml) and EtOH (1 ml). The mixture was stirred for 1.5 hours at 75° C. and allowed to cool to ambient temperature. Saturated NaHCO3 (10 ml) was added and the solution was extracted with EtOAc (100 ml). The extracts were washed with brine (40 ml) and dried. The volatile material was removed by evaporation. The reaction had not gone to completion, so additional iron (324 mg) and conc. hydrochloric acid (3 drop) was added to a suspension of the residue in water (0.25 ml) and EtOH (1 ml). The mixture was stirred for 3 hours at 75° C. After the mixture was allowed to cool to ambient temperature, saturated NaHCO3 (10 ml) was added and the solution was extracted with EtOAc (100 ml). The extracts were washed with brine (40 ml) and dried. The volatile material was removed by evaporation to give a foam. This was purified by chromatography on silica gel, eluted with 4% MeOH in DCM to give the title compound as a foam (250 mg). NMR: 1.58 (s, 3H), 2.81 (s, 3H), 2.95 (s, 3H), 6.31 (s, 2), 7.60 (m, 3H), 7.81 (d, 1H), 7.96 (m, 3H), 9.73 (brs, 1H), m/z 492.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionthe solution was extracted with EtOAc (100 ml)
  3. washThe extracts were washed with brine (40 ml)
  4. customdried
  5. customThe volatile material was removed by evaporation
  6. additionwas added to a suspension of the residue in water (0.25 ml)
  7. stirringThe mixture was stirred for 3 hours at 75° C
  8. temperatureto cool to ambient temperature
  9. additionsaturated NaHCO3 (10 ml) was added
  10. extractionthe solution was extracted with EtOAc (100 ml)
  11. washThe extracts were washed with brine (40 ml)
  12. customdried
  13. customThe volatile material was removed by evaporation
  14. customto give a foam
  15. customThis was purified by chromatography on silica gel
  16. washeluted with 4% MeOH in DCM

Sources & evidence

ORD record
ord-4303c52af7cf4fa285e67827c9add68a
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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