HCID 59843290, compound → HCID 59843268, compound

HRID 2196565Notes

Reaction equation

HRID 2196565 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[O:15])=[CH:12][C:11]([C:26]([F:29])([F:28])[F:27])=[N:10]2)[CH:6]=[CH:7][CH:8]=1)=[O:2].[CH3:30][Mg]Br>C1COCC1>[OH:2][CH:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:13]([C:14]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH3:25])=[O:15])=[CH:12][C:11]([C:26]([F:28])([F:29])[F:27])=[N:10]2)[CH:6]=[CH:7][CH:8]=1)[CH3:30]

Participants

4

Reactant 2

HCID 59843290HCID 59843290, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59843268HCID 59843268, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 149 (764.1 mg, 1.894 mmol) in THF (18.9 ml) 78° C. was added drop-wise a solution of methyl magnesium bromide (1.579 ml, 4.74 mmol). The temperature was allowed to slowly warm to 0° C. and the reaction was stirred an additional hour at 0° C., then it was quenched with water and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated and the residue was purified by chromatography (Biotage, 20 to 70% EtOAc in hexane) to afford 153 (646 mg, 1.54 mmol, 87%) as peach oil. LRMS (ESI): (calc.) 419.2 (found) 442.2 (MNa)+.

Workup

  1. customit was quenched with water
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customthe residue was purified by chromatography (Biotage, 20 to 70% EtOAc in hexane)

Sources & evidence

ORD record
ord-336f40dc57e44cf7ac327afb3ab8263d
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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