Water → HCID 54222524, compound

HRID 1757058Notes

Reaction equation

HRID 1757058 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][CH:18]=[CH:19][C:20]([O:22]C)=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na].O>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 54280683HCID 54280683, compound

Product 1

HCID 54222524HCID 54222524, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 0.85 g (2.7 mmol) of methyl 5-[2-(tert-butoxycarbonylaminomethyl)phenyl]-2,4-pentadienoate, 1.17 g (11 mmol) of sodium carbinate, 15 ml of water and 15 ml of methanol was heated at reflux for 2 hours. After the produced methanol was distilled off, the solution was cooled to 0° C. and carefully acidified with 1N hydrochloric acid. The resulting mixture was extracted with methylene chloride and the extracts were washed with brine, dried (Na2SO4) and concentrated. Recrystallization of the residue from 1:3 methylene chloride:hexane gave 0.7 g (86%) of the product as crystals, mp 179°-182° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. distillationAfter the produced methanol was distilled off
  4. extractionThe resulting mixture was extracted with methylene chloride
  5. washthe extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customRecrystallization of the residue from 1:3 methylene chloride

Sources & evidence

ORD record
ord-7b738f3a0dd84c748ba538b0d289c65e
Source dataset
uspto-grants-1995_08
Patent number
US05444048

Reaction notes

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