HCID 86725303, compound → HCID 86725308, compound

HRID 925193Notes

Reaction equation

HRID 925193 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[C:12](=[O:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH:21]1([Mg]Br)[CH2:23][CH2:22]1>C(OCC)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[C:12]([CH:21]4[CH2:23][CH2:22]4)([OH:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 86725303HCID 86725303, compoundHCID 178418630HCID 178418630, compound

Product 1

HCID 86725308HCID 86725308, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Into a stirred 100 ml flask containing Intermediate 3 (200 mg, 0.732 mmol) dissolved in diethyl ether (20 ml), cyclopropylmagnesium bromide (0.5M in THF, 7.32 ml, 3.66 mmol) was added at reflux. The reaction mixture was stirred at reflux for 1 hour. The reaction mixture was allowed to cool to room temperature and was quenched by addition of 10% aq. NH4Cl (50 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the sub-titled compound which was used without further purification. MS: ESI (positive): 298, (M-OH).

Workup

  1. temperatureat reflux
  2. temperatureat reflux for 1 hour
  3. customwas quenched by addition of 10% aq. NH4Cl (50 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-2f3a3cf1d16a40c5bf6c759e5e9e7a37
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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