Hydrochloric Acid → HCID 12944586, compound

HRID 1379957Notes

Reaction equation

HRID 1379957 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-07120f6d371d4edf946bf2d7adcf8df0
Source dataset
uspto-grants-1997_09
Patent number
US05672602

Reaction notes

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