Hydrochloric Acid → HCID 22951558, compound

HRID 276722Notes

Reaction equation

HRID 276722 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH2:13][O:14][CH2:15][C@@H:16]([C:18]([NH:20]C(OC(C)(C)C)=O)=[O:19])[NH2:17])[CH:10]=[CH:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3].Cl>CCOC(C)=O>[CH2:1]([O:4][C:5]([C:7]1[CH:8]=[C:9]([CH2:13][O:14][CH2:15][C@@H:16]([C:18]([NH2:20])=[O:19])[NH2:17])[CH:10]=[CH:11][CH:12]=1)=[O:6])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69266275HCID 69266275, compound

Product 1

HCID 22951558HCID 22951558, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of O-[[3-(allyloxycarbonyl)phenyl]methyl]-N-(t-butoxycarbonyl)-L-serinamide (69 g, 182.5 mmol) in EtOAc (1000 mL) at 0° C. is slowly bubbled HCl gas for 1 hour, during which time a white precipitate is observed. The mixture is warmed to room temperature over 30 minutes, after which time EtOAc is removed by evaporation. The resulting residue is triturated with ether (500 mL) with vigorous stirring for 30 minutes. The precipitate is collected by vacuum filtration, washed with ether (2×100 mL) and then air dried to yield O-[[3-(allyloxycarbonyl)phenyl]-methyl]-L-serinamide.HCl as a free-flowing white solid.

Workup

  1. customat 0° C.
  2. customfor 1 hour
  3. customafter which time EtOAc is removed by evaporation
  4. customThe resulting residue is triturated with ether (500 mL)
  5. filtrationThe precipitate is collected by vacuum filtration
  6. washwashed with ether (2×100 mL)
  7. customair dried

Sources & evidence

ORD record
ord-2d129e8ea7fd46cfa89a95f9c97d4b5d
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

Loading…