Hydrochloric Acid → HCID 18539014, compound

HRID 412948Notes

Reaction equation

HRID 412948 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])=[CH:34][CH:33]=3)[CH2:27][CH2:26]2)[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[BH4-].[Na+].Cl.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][C:32]3[CH:33]=[CH:34][C:35]([CH:38]([OH:42])[CH:39]([CH3:40])[CH3:41])=[CH:36][CH:37]=3)[CH2:27][CH2:26]2)[C:10]([CH:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:19])=[O:20])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 18539212HCID 18539212, compound

Product 1

HCID 18539014HCID 18539014, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the title compound of example 335 (318 mg, 0.50 mmol) in a mixture of methanol (5 mL) and THF (5 mL) was added sodium borohydride (38 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 16 hours before the addition of 1N hydrochloric acid (2 mL). After being stirred at room temperature for 30 minutes, 1N aqueous sodium hydroxide (4 mL) was added and the mixture was evaporated under reduced pressure. Water (15 mL) was added and extracted with dichloromethane (30 mL, 2×15 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. A mixture of ethanol and ethyl acetate was added to the residue, the resulting precipitate was collected by filtration, washed with ethyl acetate and dried under reduced pressure to afford the title compound (280 mg, 0.44 mmol, yield 88%) as a white solid.

Workup

  1. customthe mixture was evaporated under reduced pressure
  2. additionWater (15 mL) was added
  3. extractionextracted with dichloromethane (30 mL, 2×15 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. additionA mixture of ethanol and ethyl acetate
  8. additionwas added to the residue
  9. filtrationthe resulting precipitate was collected by filtration
  10. washwashed with ethyl acetate
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-0121086e1fbb448eab4370c0944720c3
Source dataset
uspto-grants-2003_05
Patent number
US06562978B1

Reaction notes

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