Dibah → HCID 10229091, compound

HRID 896675Notes

Reaction equation

HRID 896675 reaction equation
C[O:2][C:3](=O)[CH:4]([C:29]1[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]([C:22]([S:25]([CH3:28])(=[O:27])=[O:26])([CH3:24])[CH3:23])[CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][CH:18]=[CH:17]3)[CH:7]=1.CC(C[Al]CC(C)C)C>C(Cl)Cl>[CH3:28][S:25]([C:22]([C:14]1[CH:15]=[C:16]2[C:21](=[C:12]([C:8]3[CH:7]=[C:6]([CH2:5][CH:4]([C:29]4[CH:34]=[CH:33][C:32]([S:35][CH3:36])=[CH:31][CH:30]=4)[CH2:3][OH:2])[CH:11]=[CH:10][CH:9]=3)[CH:13]=1)[N:20]=[CH:19][CH:18]=[CH:17]2)([CH3:24])[CH3:23])(=[O:26])=[O:27]

Participants

4

Reactant 2

HCID 16682954DibahHCID 69693298HCID 69693298, compound

Product 1

HCID 10229091HCID 10229091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of the ester from Step 1, Example 13 (1.0 g, 5 mmol) in CH2Cl2 (25 mL) at −78° C. was added dibal-H (20.1 mL, 12 mmol). The resulting reaction mixture was warmed slowly to 21° C., then quenched with sodium potassium tartrate solution and stirred at 21° C. for 3 h. The reaction mixture was diluted with ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 50:50) provided the title compound as a white foam.

Workup

  1. customThe resulting reaction mixture
  2. customquenched with sodium potassium tartrate solution
  3. additionThe reaction mixture was diluted with ethyl acetate
  4. washThe organic extracts were washed (H2O), (brine),
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washby flash chromatography (eluting with hexane/ethyl acetate, 50:50)

Sources & evidence

ORD record
ord-e4011debe16a4f2c8741f68da78748dd
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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