Hydrochloric Acid → HCID 12944586, compound

HRID 235533Notes

Reaction equation

HRID 235533 reaction equation
C[O:2][C:3](=[O:23])[CH:4]([N:12]([CH2:20][CH:21]=[CH2:22])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[C:16]([O:15][C:13]([N:12]([CH2:20][CH:21]=[CH2:22])[C@@H:4]([CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:23])=[O:2])=[O:14])([CH3:17])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57206988N-(t-butoxycarbonyl)-allylamino-3-phenyl-propionic acid methyl ester

Product 1

HCID 12944586HCID 12944586, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine (S)-2-[N-(t-butoxycarbonyl)-allylamino-3-phenyl-propionic acid methyl ester (0.32 g, 1.0 mmol) and 1M sodium hydroxide (10 mL, 10 mmol) in ethanol (10 mL). Stir for 4 hours. Acidify the reaction mixture with 1M hydrochloric acid and extract with ethyl acetate. Separate the layers, dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph on silica gel eluting with 3% methanol/dichloromethane to give the title compound: TLC Rf =0.40 (silica gel, 5% methanol/dichloromethane).

Workup

  1. extractionextract with ethyl acetate
  2. customSeparate the layers
  3. dry with materialdry the organic layer over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo

Sources & evidence

ORD record
ord-8f4d8671ab594270909a3367a1c62372
Source dataset
uspto-grants-1997_01
Patent number
US05597845

Reaction notes

Loading…