Water → HCID 9866922, compound

HRID 1828249Notes

Reaction equation

HRID 1828249 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][C:21](=[O:23])[C:20]4[N:24]([CH3:27])[CH:25]=[CH:26][C:19]=4[S:18]3(=[O:29])=[O:28])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH:21]([OH:23])[C:20]4[N:24]([CH3:27])[CH:25]=[CH:26][C:19]=4[S:18]3(=[O:29])=[O:28])[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 9845047HCID 9845047, compound

Product 1

HCID 9866922HCID 9866922, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 42 mg (0.1 mmol) of Compound 21 in 5 ml of ethanol, 38 mg (1 mmol) of sodium borohydride were added gradually under ice-cooled stirring. The resulting mixture was stirred under ice cooling for 1 hour and further at room temperature for 13 hours. Water (5 ml) was added to the reaction mixture. The thus-obtained mixture was stirred at room temperature for 5 hours and then concentrated under reduced pressure. Post treatment and purification were conducted as in Example 15, whereby 36 mg of the title compound were obtained (yield: 85%).

Workup

  1. additionwere added gradually under ice-
  2. temperaturecooled
  3. stirringThe resulting mixture was stirred under ice cooling for 1 hour and further at room temperature for 13 hours
  4. stirringThe thus-obtained mixture was stirred at room temperature for 5 hours
  5. concentrationconcentrated under reduced pressure
  6. customPost treatment and purification

Sources & evidence

ORD record
ord-45b82e943cc244d8ad3264df60b403ee
Source dataset
uspto-grants-2006_06
Patent number
US07057036B2

Reaction notes

Loading…