HCID 10783725, compound → HCID 21893558, compound

HRID 1358656Notes

Reaction equation

HRID 1358656 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)=[O:2].[CH3:25][Mg]Br>O1CCCC1.C(OCC)C.O>[OH:2][CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([CH3:24])[CH2:16][NH:17][S:18]([CH:21]([CH3:23])[CH3:22])(=[O:19])=[O:20])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)[CH3:25]

Participants

6

Reactant 2

HCID 10783725HCID 10783725, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21893558HCID 21893558, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.2 g (0.4 mmol) of material from Example 45 in 3 mL of tetrahydrofuran at ambient temperature was added 0.3 mL (0.9 mmol) of a 3.0M solution of methylmagnesium bromide in ethyl ether. The mixture was stirred for 16 hours, diluted with 5 mL of water and extracted four times with 5 mL each of ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Chromatography (10 g silica gel, 45% ethyl acetate/hexane) of the residue afforded 0.1 g (74%) of the title compound.

Workup

  1. extractionextracted four times with 5 mL each of ethyl acetate
  2. dry with materialThe combined organics were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1d341ceafe6494a8c23c3af84715688
Source dataset
uspto-grants-2003_07
Patent number
US06596716B2

Reaction notes

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