Water → HCID 54406649, compound

HRID 1736613Notes

Reaction equation

HRID 1736613 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]([O:20]C)=[O:19])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].O>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:18]([OH:20])=[O:19])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 54369085HCID 54369085, compound

Product 1

HCID 54406649HCID 54406649, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

After a stirred mixture of 4.06 g (14 mmol) of methyl 3-[3-(tert-butoxycarbonyl aminomethyl)phenyl]-2-propenoate, 3.0 g (28.3 mmol) of sodium carbonate, 75 ml of water and 75 ml of methanol was heated at reflux for 5 hours, the produced methanol was distilled off and the solution was cooled to 0° C. and acidified with 1N hydrochloric acid. The resulting mixture was extrated with ethyl acetate. The extracts were washed with brine, dried (Na2SO4) and concentrated. Recrystallization of the residual solid from 1:3 ethyl acetate-hexane gave 3.52 g (91%) of the product as crystals, mp 121°-123° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 hours
  3. distillationthe produced methanol was distilled off
  4. washThe extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customRecrystallization of the residual solid from 1:3 ethyl acetate-hexane

Sources & evidence

ORD record
ord-edc702ef178e4c5e92811ea3eb7f3948
Source dataset
uspto-grants-1996_07
Patent number
US05541286

Reaction notes

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