Hydrochloric Acid → HCID 10265595, compound

HRID 1682434Notes

Reaction equation

HRID 1682434 reaction equation
C[O:2][C:3](=[O:21])[C@H:4]([CH2:16][O:17][CH2:18][CH:19]=[CH2:20])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[OH-].[Li+].Cl>C(O)C>[CH2:9]([O:8][C:6]([NH:5][C@H:4]([C:3]([OH:21])=[O:2])[CH2:16][O:17][CH2:18][CH:19]=[CH2:20])=[O:7])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 13995645HCID 13995645, compound

Product 1

HCID 10265595HCID 10265595, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve N-(benzyloxycarbonyl)-O-2-propenyl-L-serine methyl ester (21.7 mmol) in ethanol (150 mL. Add 1N lithium hydroxide (50 mL) and stir overnight at room temperature. Reflux for 1 hour, cool to -10°, carefully adjust to pH 4 with 1N hydrochloric acid and stir for 1 hour. Extract into ethyl acetate, dry (MgSO4) and evaporate the solvent in vacuo to give N-(benzyloxycarbonyl)-O-2-propenyl-L-serine.

Workup

  1. temperatureReflux for 1 hour
  2. temperaturecool to -10°
  3. stirringstir for 1 hour
  4. extractionExtract into ethyl acetate
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-3333ddd18beb4298b7b0de225a4ba192
Source dataset
uspto-grants-1997_06
Patent number
US05635502

Reaction notes

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