Magnesium → HCID 131732178, compound

HRID 1486156Notes

Reaction equation

HRID 1486156 reaction equation
[CH2:1]([N:8]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:9]([C@H:11]1[C@H:16]([C:17](=[O:33])[N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][CH2:14][C:13](=[CH:34][C:35]([O:37][CH2:38]C)=[O:36])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg]>CO>[CH2:40]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]([C@H:11]1[C@H:16]([C:17](=[O:33])[N:18]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:15][CH2:14][C@@H:13]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:12]1)=[O:10])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 5462224Magnesium2×HCID 86722950HCID 86722950, compound

Product 1

HCID 131732178HCID 131732178, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Ethyl 2-[(trans)-3,4-bis(dibenzylcarbamoyl)cyclohexylidene]acetate (9.27 g, 15 mmol) in dry MeOH (75 mL) is added Magnesium ribbon (1.08 g, 45 mmol). The suspension was stirred for 5 hr. To this homogeneous solution is added a further batch of Magnesium ribbon (200 mg, 8.2 mmol). This mixture is stirred for 17 hr. The resulting solution is extracted with EtOAc, washed with brine, dried over MgSO4 and concentrated. The residue is purified by silica chromatography (eluting with 20% ethyl acetate/10% dichloromethane in hexane) to give the title compound (8.27 g) as a foam. ESI-MS (m/z) 617 (MH)+.

Workup

  1. stirringThis mixture is stirred for 17 hr
  2. extractionThe resulting solution is extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by silica chromatography (eluting with 20% ethyl acetate/10% dichloromethane in hexane)

Sources & evidence

ORD record
ord-5570cb5a2590452f97a3518f046d66b8
Source dataset
uspto-grants-2016_08
Patent number
US09422314B2

Reaction notes

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