Sodium Hydroxide → 281233-84-9

HRID 1264246Notes

Reaction equation

HRID 1264246 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO.O>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 18617679Methyl 4-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-propyn-1-yl]benzoate

Product 1

HCID 18617833281233-84-9Yield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Methyl 4-(3-t-butoxycarbonylaminoprop-1-ynyl)benzoate (1.09 g, 38 mmol, reference example 81) is dissolved in MeOH (15 mL) and to this solution added NaOH (0.15 g, 38 mmol) dissolved in water (5 mL). This mixture is heated to reflux. After 5 hours, the solvent is removed in vacuo and CH2Cl2 and 1N HCl added to the residue. The organic layer is washed with 1N HCl, water and brine, then dried over magnesium sulfate. The solvent is removed in vacuo to give a white solid (0.60 g, 57% yield): 1H NMR (300 MHz, CD3OD) d 7.86 (d, 2H), 7.39 (d, 2H), 3.98 (s, 2H), 1.38 (s, 9H).

Workup

  1. temperatureThis mixture is heated to reflux
  2. customthe solvent is removed in vacuo and CH2Cl2 and 1N HCl
  3. additionadded to the residue
  4. washThe organic layer is washed with 1N HCl, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-61fac28685f84f5ba6fee96cae82cda9
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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