Sodium Methoxide → HCID 59608423, compound

HRID 2067159Notes

Reaction equation

HRID 2067159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C(=O)C(C)(C)C)=[CH:4][C:3]=1[C:15]([NH:17][CH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:16].C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:15]([NH:17][CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1)=[O:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 59608436HCID 59608436, compound

Product 1

HCID 59608423HCID 59608423, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-{[({2-chloro-5-[(2,2-dimethylpropanoyl)oxy]phenyl}carbonyl)amino]methyl}benzoate (590 mg, 1.46 mmol) and sodium methoxide (1.2 eq, 95 mg, 1.76 mmol) in methanol (10 ml) was heated at 65° C. overnight. On cooling the solvent was evaporated in vacuo to give the title compound as a white solid. MS (ES+) m/z 320 [M+H]+ (C16H1435ClNO4). 1H-NMR (400 MHz, d6-DMSO) δ 3.84 (3H, s), 4.45 (2H, d, J 6), 6.55 (2H, m), 6.99 (1H, d, J 8.8), 7.46 (2H, d, J 8.4), 7.92 (2H, m), 8.82 (1H, t).

Workup

  1. temperatureOn cooling the solvent
  2. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-b3024deb43254d7180865006feb2f14c
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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