HCID 59389278, compound → HCID 59389404, compound

HRID 2357921Notes

Reaction equation

HRID 2357921 reaction equation
C[Mg]Br.O1CCC[CH2:5]1.[CH:9]([C:11]1[CH:29]=[C:14]2[C:15]([C:21]3[CH:22]([CH3:28])[CH2:23][C:24](=[O:27])[NH:25][N:26]=3)=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[N:13]2[N:12]=1)=[O:10]>C1COCC1>[OH:10][CH:9]([C:11]1[CH:29]=[C:14]2[C:15]([C:21]3[CH:22]([CH3:28])[CH2:23][C:24](=[O:27])[NH:25][N:26]=3)=[CH:16][CH:17]=[C:18]([O:19][CH3:20])[N:13]2[N:12]=1)[CH3:5]

Participants

4

Reactant 2

HCID 59389278HCID 59389278, compoundHCID 178420675HCID 178420675, compound

Product 1

HCID 59389404HCID 59389404, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 0.90 mol/L methyl magnesium bromide-tetrahydrofuran solution (0.878 mL) was added dropwise to a solution of the compound of Example 237 (90.6 mg) in THF (15 mL) at −78° C. in an argon atmosphere. The mixture was allowed to gradually warm to room temperature. The reaction was quenched by adding a saturated aqueous solution of ammonium chloride and the mixture was extracted with THF (100 mL). The extract was washed with water and saturated brine and dried over anhydrous sodium sulfate. The dried extract was concentrated and purified by recrystallization (methanol-ethyl acetate-hexane) to afford the title compound as a pale yellow powder (38.0 mg).

Workup

  1. customThe reaction was quenched
  2. additionby adding a saturated aqueous solution of ammonium chloride
  3. extractionthe mixture was extracted with THF (100 mL)
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. extractionThe dried extract
  7. concentrationwas concentrated
  8. custompurified by recrystallization (methanol-ethyl acetate-hexane)

Sources & evidence

ORD record
ord-78e704d923f24aaeb25d31892cfddfe1
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

Loading…