Water → HCID 23017092, compound

HRID 1726319Notes

Reaction equation

HRID 1726319 reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][CH:4]([NH:12][C:13]([C:15]1[CH:20]=[C:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:18]=[CH:17][C:16]=1[CH2:29][CH2:30][C:31](O)=[O:32])=[O:14])[C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.B#B.O>O1CCCC1>[CH3:1][CH:2]([CH3:34])[CH2:3][CH:4]([NH:12][C:13]([C:15]1[CH:20]=[C:19]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:18]=[CH:17][C:16]=1[CH2:29][CH2:30][CH2:31][OH:32])=[O:14])[C:5]1[CH:6]=[CH:7][C:8]([F:11])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6328200DiboronHCID 23016797HCID 23016797, compound

Product 1

HCID 23017092HCID 23017092, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 6(40) (2.00 g) in tetrahydrofuran (5 ml) was added dropwise diborane (1M solution in tetrahydrofuran, 8.6 ml) at 0° C. under an atmosphere of argon. The mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate and concentrated. The residue was washed with hexane-ethyl acetate to give the title compound (1.67 g) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride subsequently, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with hexane-ethyl acetate

Sources & evidence

ORD record
ord-501cab2e887e41e98d5d354e04ed8811
Source dataset
uspto-grants-2009_02
Patent number
US07491748B2

Reaction notes

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