Water → HCID 22225254, compound

HRID 1744799Notes

Reaction equation

HRID 1744799 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:28]=[CH:27][C:11]([NH:12][C:13]2[C:18]([C:19](OCC)=[O:20])=[C:17]([CH3:24])[N:16]=[C:15]([S:25][CH3:26])[N:14]=2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>C(O)C>[OH:20][CH2:19][C:18]1[C:13]([NH:12][C:11]2[CH:27]=[CH:28][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:9][CH:10]=2)=[N:14][C:15]([S:25][CH3:26])=[N:16][C:17]=1[CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11524223HCID 11524223, compound

Product 1

HCID 22225254HCID 22225254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of compound E (30 g; 0.0743 mol) in 500 mL of anhydrous ethanol at 45° C. NaBH4 (15 g; 0.397 mol) was added portion-wise under vigorous stirring. After 4 h the reaction mixture was brought to room temperature and was poured into 2 L of iced water, vigorously stirred for 10′ and extracted with ethyl acetate (2×600 mL). The organic phase was washed with water until neutral pH, with brine and dried over anhydrous sodium sulphate. After evaporation the crude compound F (22 g; 82%) was used without further purification in the next step.

Workup

  1. extractionextracted with ethyl acetate (2×600 mL)
  2. washThe organic phase was washed with water until neutral pH, with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customAfter evaporation the crude compound F (22 g; 82%)
  5. customwas used without further purification in the next step

Sources & evidence

ORD record
ord-8c06d2d8b47346d6b654517939a40eec
Source dataset
uspto-grants-2006_03
Patent number
US07019002B2

Reaction notes

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