HCID 42625373, compound → HCID 42625375, compound

HRID 1174319Notes

Reaction equation

HRID 1174319 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([N:13]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[N:24]=[C:23]([C:25]([O:27]C)=O)[CH:22]=[CH:21][CH:20]=2)[C:14]1=[O:29])[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][Mg]Br>O1CCCC1.C(OCCCC)CCC>[C:25]([C:23]1[N:24]=[C:19]([CH2:18][N:15]2[CH2:16][CH2:17][N:13]([C@@H:8]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C:14]2=[O:29])[CH:20]=[CH:21][CH:22]=1)(=[O:27])[CH3:30]

Participants

5

Reactant 2

HCID 42625373HCID 42625373, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 42625375HCID 42625375, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8909Butyl etherSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of the product from Example 17D (1.95 g, 4.815 mmol) in tetrahydrofuran (50 mL) at −78° C. was treated methylmagnesium bromide in butyl ether (5.7 mL, 1 M). The mixture was stirred 0.5 hours at −78° C., quenched with acetone (3 mL) and 10% citric acid. The reaction mixture was partitioned between ethyl acetate and 1 N NaHCO3, and the organic phase layer was decanted and concentrated. The residue was purified by flash chromatography on silica gel eluting with 25%-50% ethyl acetate in hexane give the title compound (1.6 g, 85% yield).

Workup

  1. customquenched with acetone (3 mL) and 10% citric acid
  2. customThe reaction mixture was partitioned between ethyl acetate and 1 N NaHCO3
  3. customthe organic phase layer was decanted
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography on silica gel eluting with 25%-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-15d7493b671345dd85fae39c6eb1bce7
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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