Hydrochloric Acid → HCID 86739452, compound

HRID 1262532Notes

Reaction equation

HRID 1262532 reaction equation
C[O:2][C:3](=[O:21])[CH:4]([CH2:19][Cl:20])[NH:5][C:6](=[O:18])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH:16]=[CH2:17])=[CH:10][CH:9]=1.[OH-].[Na+].Cl>CC(C)=O>[CH2:15]([O:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C:6]([NH:5][CH:4]([C:3]([OH:21])=[O:2])[CH2:19][Cl:20])=[O:18])=[CH:13][CH:12]=1)[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 77975665HCID 77975665, compound

Product 1

HCID 86739452HCID 86739452, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

4-Allyloxy-3-chloro-phenylacetyl-(DL)-alanine methyl ester (2.0 g) was suspended in acetone (20 ml). Aqueous sodium hydroxide (1 M, 8.0 ml) was added and the mixture was gently warmed to effect solution, and then heated to 40° C. for 20 min. After the solution has been cooled, the pH was adjusted to 2-3 using dilute hydrochloric acid (3 M) and the product was extracted with ethyl acetate (40 ml). The extract was dried (anhydrous sodium sulphate). The solvent was evaporated at reduced pressure to leave a solid residue (1.8 g); it had m.p. 120°-124° C. After recrystallisation from ethyl acetate/light petroleum (b.p. 60°-80° C.) the above-named product, (1.6 g), m.p. 123°-124° C. was obtained.

Workup

  1. temperaturethe mixture was gently warmed
  2. temperatureAfter the solution has been cooled
  3. extractionthe product was extracted with ethyl acetate (40 ml)
  4. dry with materialThe extract was dried (anhydrous sodium sulphate)
  5. customThe solvent was evaporated at reduced pressure

Sources & evidence

ORD record
ord-343b8222f2284c43b3d806f2fe857d70
Source dataset
uspto-grants-1984_06
Patent number
US04452783

Reaction notes

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