Sodium Carbonate → HCID 89647654, compound

HRID 2175395Notes

Reaction equation

HRID 2175395 reaction equation
[C:1]([O-])([O-])=O.[Na+].[Na+].[Cl:7][C:8]1[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=1)[CH2:11][C@H:12]([C:14]([OH:16])=[O:15])[NH2:13].Cl[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CO.O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:17](=[CH:18][CH:19]=1)[CH2:1][N:13]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C@@H:12]([C:14]([OH:16])=[O:15])[CH2:11]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10928Ethyl chloroformateHCID 70094093-Chloro-D-phenylalanine

Product 1

HCID 89647654HCID 89647654, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Na2CO3 (2.12 g, 20.04 mmol) was added to a suspension of 3-chloro-D-phenylalanine 9 (2.6 g, 10.02 mmol) in MeOH/H2O (8.3 mL/8.3 mL) at room temperature. Ethyl chloroformate (1.44 mL, 15.03 mmol) was added drop wise over 20 min via syringe pump and the reaction was stirred overnight. The reaction mixture was washed with Et2O (1×15 mL) and the aqueous layer was acidified to pH ˜5 with 2 M HCl (aq). The aqueous layer was extracted with EtOAc (2×30 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to obtain the ethyl carbamate.

Workup

  1. washThe reaction mixture was washed with Et2O (1×15 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (2×30 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9af57227ae194a44a834b854a7c61f9d
Source dataset
uspto-grants-2015_06
Patent number
US09062071B2

Reaction notes

Loading…