HCID 59556133, compound → HCID 59556152, compound

HRID 1809941Notes

Reaction equation

HRID 1809941 reaction equation
[O:1]=[C:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([N:10]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11]1)[CH2:6]2.[C:23]1([Mg]Br)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[OH:1][C:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([N:10]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH2:11]1)[CH2:6]2

Participants

4

Reactant 2

HCID 59556133HCID 59556133, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 59556152HCID 59556152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of the ketone obtained in Step B (65 mg, 0.21 mmol) in THF (2 mL) cooled in an ice bath was added a 1 M solution of phenyl magnesium bromide in THF (0.25 mL). After being stirred at −78° C. for 3 hours, the reaction was quenched with aqueous ammonium chloride. The resulting solution was extracted with EtOAc 3 times. The combined EtOAc layers were dried over MgSO4 and concentrated. Flash chromatography on silica gel eluting with 5%, 10% and 50% MeOH/CH2Cl2 provided 27 mg of the title compound as a mixture of two isomers (7:3). MS calculated (M+H)+387. Found 387.1.

Workup

  1. customthe reaction was quenched with aqueous ammonium chloride
  2. extractionThe resulting solution was extracted with EtOAc 3 times
  3. dry with materialThe combined EtOAc layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a14a36323948439aa896abd0e3a00cd9
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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