Sodium Hydroxide → HCID 58683732, compound

HRID 1991057Notes

Reaction equation

HRID 1991057 reaction equation
C[O:2][C:3](=[O:21])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].[OH-].[Na+]>CO>[C:17]([O:16][C:14]([NH:13][C:7]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:6]=1/[CH:5]=[CH:4]/[C:3]([OH:21])=[O:2])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58683692HCID 58683692, compound

Product 1

HCID 58683732HCID 58683732, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(E)-3-(2-tert-Butyloxycarbonylamino-5-chlorophenyl)-acrylic acid methyl ester (1.8 g, 5.77 mmol) was dissolved in MeOH (115 ml), 2N NaOH (4.3 ml, 8.6 mmol) added and stirred at 60°C. for 2 hours. The reaction mixture was evaporated to dryness, acidified to pH 3.5 by adding water (200 ml) and 2N HCl (4.35 ml) and extracted twice with TBME. The combined organic phases were dried over Na2SO4 and evaporated to dryness to yield the title acid as a solid, which was recrystallised from TBME/hexanes to render the title compound as colorless crystals (1.0 g, 59%).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionby adding water (200 ml) and 2N HCl (4.35 ml)
  3. extractionextracted twice with TBME
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-57231acedd2c4a2f9afe946f21e3c24d
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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