Acetic Acid → HCID 20562339, compound

HRID 848143Notes

Reaction equation

HRID 848143 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[NH:10][CH2:11][C:12](=[O:40])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH2:25][CH2:26][O:27]C(=O)C)=[O:23])=[CH:17][C:16]=1[C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].C(O)(=O)C>CO>[CH2:1]([O:8][C:9](=[O:41])[NH:10][CH2:11][C:12](=[O:40])[NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH2:25][CH2:26][OH:27])=[O:23])=[CH:17][C:16]=1[C:31](=[O:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[F:38])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 20562350HCID 20562350, compound

Product 1

HCID 20562339HCID 20562339, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

250 mg of benzyl{[[2-(o-fluorobenzoyl)-4-[3-(2-acetoxyethyl)ureido]phenyl]methylcarbamoyl]methyl}carbamate dissolved in 10 ml of absolute methanol are treated with 50 mg of sodium methylate, stirred at room temperature for 1 hour and buffered with a small amount of acetic acid. The mixture is poured on to ice/10% sodium bicarbonate and extracted with methylene chloride. The organic solution is dried over sodium sulphate, filtered and concentrated. After crystallisation from ether/ethanol, there is obtained benzyl{[[2-(o-fluorobenzoyl)-4-[3-(2-hydroxyethyl)ureido]phenyl]methylcarbamoyl]methyl}carbamate which melts at 117°-120° C.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic solution is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customAfter crystallisation from ether/ethanol

Sources & evidence

ORD record
ord-fcc76a33f5884990abfe791573cee17d
Source dataset
uspto-grants-1981_10
Patent number
US04294758

Reaction notes

Loading…