Sodium Methoxide → HCID 86618208, compound

HRID 1669512Notes

Reaction equation

HRID 1669512 reaction equation
[C:1]([O:5][C:6](=[O:40])[NH:7][C@H:8]([CH2:31][N:32]([O:36]C(=O)C)[C:33](=[O:35])[CH3:34])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([O:5][C:6](=[O:40])[NH:7][C@H:8]([CH2:31][N:32]([C:33](=[O:35])[CH3:34])[OH:36])[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)=[CH:19][CH:18]=2)=[CH:14][CH:15]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86618209HCID 86618209, compound

Product 1

HCID 86618208HCID 86618208, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product from step 2 (0.12 g, 0.21 mmol) in methanol (5 mL) was added NaOMe (25% in MeOH, 0.23 g, 1.1 mmol) at 0° C. and stirred at room temperature for 4 h. After the methanol was removed, the residue was partitioned in EtOAc/H2O, dried over Na2SO4 and concentrated to yield the title compound (0.1 g, 90%). 1HNMR (CDCl3) δ 1.40 (s, 9H), 2.10 (s, 3H), 2.81 (m, 2H), 3.05 (m, 1H), 4.11 (m, 1H), 4.01 (br, 1H), 4.66 (m, 1H), 6.91 (m, 4H), 6.98 (s, 4H), 7.14 (d, J=8 Hz, 2H), 7.27 (d, J=8 Hz, 2H), MS m/z 427 (M−100).

Workup

  1. customAfter the methanol was removed
  2. customthe residue was partitioned in EtOAc/H2O
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10e4afd253cd491380d029f12cbf27e4
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

Loading…