Water → HCID 58392230, compound

HRID 561607Notes

Reaction equation

HRID 561607 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)([CH3:15])[CH2:9][C:10](OCC)=[O:11])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1.ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:16]2[C:24]3[C:19](=[C:20]([CH2:25][S:26][CH3:27])[CH:21]=[CH:22][CH:23]=3)[NH:18][CH:17]=2)([CH3:15])[CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 58392426HCID 58392426, compound

Product 1

HCID 58392230HCID 58392230, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 740 mg (1.84 mmol) of the compound from Example 104A in 20 ml of tetrahydrofuran was added dropwise to 5.5 ml (5.5 mmol) of a 1N solution of diisobutylaluminum hydride in dichloromethane in 20 ml of tetrahydrofuran at RT under argon. The mixture was stirred at RT for 2 h and then water and dichloromethane were added, and the phases were separated. The aqueous phase was extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient). 437 mg (66% of theory) of the title compound were obtained.

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-09735d6cf1794adb9161991344aef5df
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

Loading…