Benzyl chloroformate → HCID 10859837, compound

HRID 429887Notes

Reaction equation

HRID 429887 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH2:7][CH:8]([NH2:12])[C:9]([OH:11])=[O:10])=[O:5].C([O-])(O)=O.[Na+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O>[CH2:22]([O:21][C:19]([NH:12][C@H:8]([C:9]([OH:11])=[O:10])[CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 142411119-33-1HCID 516892Sodium Bicarbonate

Product 1

HCID 10859837HCID 10859837, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A 2 L 3-necked flask equipped with a magnetic stirrer and a thermometer was charged with 25.0 g of glutamic acid γ-ethyl ester (Sigma Chemical Co., St. Louis, Mo., 63178) and 1 L of distilled water. The solution was heated to 60° C. with stirring and treated with 30 g of NaHCO3 followed by 25 mL of benzyl chloroformate (Aldrich). The flask was allowed to cool to RT and stirring was continued for 2 h. The mixture was extracted with ethyl ether (5×100 mL) and the ether extracts were discarded. The aqueous phase was acidified to a congo red end point by addition of concentrated aqueous HCl and the resulting emulsion was extracted with CH2Cl2 (5×100 mL). The combined CH2Cl2 extracts were washed with 0.05 N aqueous HCl (2×100 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to a volume of 50 mL. The solution was chilled in an ice water bath and triturated with addition of 200 mL of pentane. The resulting solid was collected by vacuum filtration and dried in vacuo to afford 37.0 g (83%) of N-((benzyloxy)carbonyl)5-O-ethyl-L-glutamic acid as a white powder, m.p. 82-84° C.

Workup

  1. customA 2 L 3-necked flask equipped with a magnetic stirrer
  2. temperatureto cool to RT
  3. stirringstirring
  4. extractionThe mixture was extracted with ethyl ether (5×100 mL)
  5. additionThe aqueous phase was acidified to a congo red end point by addition of concentrated aqueous HCl
  6. extractionthe resulting emulsion was extracted with CH2Cl2 (5×100 mL)
  7. washThe combined CH2Cl2 extracts were washed with 0.05 N aqueous HCl (2×100 mL)
  8. dry with materialdried over anhydrous Na2SO4
  9. concentrationconcentrated in vacuo to a volume of 50 mL
  10. temperatureThe solution was chilled in an ice water bath
  11. customtriturated with addition of 200 mL of pentane
  12. filtrationThe resulting solid was collected by vacuum filtration
  13. customdried in vacuo

Sources & evidence

ORD record
ord-b96cc82e9b2f4de19391a48ebf30063d
Source dataset
uspto-grants-2001_11
Patent number
US06319702B1

Reaction notes

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