Sodium borohydride → HCID 67316103, compound

HRID 1013165Notes

Reaction equation

HRID 1013165 reaction equation
[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[N:18]=2)=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[S:19](=[O:27])(=[O:26])[NH:18]2)=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 67315890HCID 67315890, compound

Product 1

HCID 67316103HCID 67316103, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the product from example 1, step c (100 mg, 0.25 mmol) was dissolved in 4 mL MeOH. NaBH4 (30 mg, 0.75 mmol) was added and the reaction was stirred at rt for ½ h. Additional NaBH4 was added as needed in order to push the reaction to completion. The reaction was carefully quenched with HOAc until the evolution of hydrogen ceased. The resulting solution was partitioned between dichloromethane (DCM) and H2O. The organic layer was dried over MgSO4 and concentrated to an orange oil that was used without further purification. MS: ESI (negative): 397 (M−H).

Workup

  1. customthe reaction to completion
  2. customThe reaction was carefully quenched with HOAc until the evolution of hydrogen
  3. customThe resulting solution was partitioned between dichloromethane (DCM) and H2O
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated to an orange oil that
  6. customwas used without further purification

Sources & evidence

ORD record
ord-3a8607a90fb444c0bd8f18e6b50a2bd5
Source dataset
uspto-grants-2011_07
Patent number
US07981912B2

Reaction notes

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