HCID 131728981, compound → HCID 131728980, compound

HRID 2428191Notes

Reaction equation

HRID 2428191 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@@H:6]2[N:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:9]([CH2:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[Cl:30])=[CH:14][CH:13]=1)[CH2:8][CH2:7]2)=[O:4]>CO>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:23]([Cl:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=3[Cl:28])=[CH:14][CH:13]=2)[CH2:10][C@H:9]2[N:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@@H:6]1[CH2:7][CH2:8]2)=[O:4]

Participants

3

Reactant 1

HCID 131728981HCID 131728981, compound

Product 1

HCID 131728980HCID 131728980, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mg (1.02 g, 41.8 mmol) was added to a sol. of compound C2 (4.70 g, 8.36 mmol) in MeOH (230 mL). The reaction mixture was stirred at rt for 2 h. Mg (1.02 g, 41.8 mmol) was added again, and the mixture was stirred for 2 h again. The reaction mixture was heated to 70° C. and stirred at this temperature for 16 h. The mixture was allowed to cool down to rt, and was quenched with aq. sat. NH4Cl (5 mL). EtOAc was added, and the mixture was washed with water (2×) and brine (1×). The org. phase was dried over MgSO4, filtered, and concentrated under reduced pressure. Purification of the crude by FC (EtOAc/heptane 5:45→6:44→7:43→8:42) yielded the title compound (595 mg, 13%). LC-MS: tR=1.18 min; ES+: 564.18.

Workup

  1. stirringthe mixture was stirred for 2 h again
  2. temperatureThe reaction mixture was heated to 70° C.
  3. stirringstirred at this temperature for 16 h
  4. temperatureto cool down to rt
  5. customwas quenched with aq. sat. NH4Cl (5 mL)
  6. additionEtOAc was added
  7. washthe mixture was washed with water (2×) and brine (1×)
  8. dry with materialphase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customPurification of the crude by FC (EtOAc/heptane 5:45→6:44→7:43→8:42)

Sources & evidence

ORD record
ord-99e72909caff403ca82d7723c00d14c1
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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