Sarcosine → N-Carbobenzoxysarcosine

HRID 1413337Notes

Reaction equation

HRID 1413337 reaction equation
[NH:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2].Cl[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]>[OH-].[Na+]>[C:12]1([CH2:11][O:10][C:8]([N:1]([CH2:3][C:4]([OH:6])=[O:5])[CH3:2])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 1088SarcosineHCID 10387Benzyl chloroformate

Product 1

HCID 97053N-CarbobenzoxysarcosineYield 95.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

This material was prepared following the method of R. S. Tipton and B. A. Pawson [J. Org. Chem., 26, 4648 (1961)]. Sarcosine (8.90 g, 1.0 mole) was dissolved in 500 ml of 2 N sodium hydroxide with cooling in an ice bath. Simultaneously, 550 ml of 2 N sodium hydroxide and benzyl chloroformate [196 g (95%), 1.095 moles] were added over a period of one hour with rapid stirring. The resulting reaction mixture was stirred for about 18 hours at ambient temperature, after which time it was extracted with three 250 ml portions of diethyl ether. Ethyl acetate (500 ml) was then added to the aqueous phase, followed by the careful addition of 200 ml of concentrated hydrochloric acid. The organic layer was separated, washed with two 500 ml portions of water followed by 300 ml of saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure after removal of the drying agent by filtration gave 213 g (95%) of N-phenylmethoxycarbonyl-sarcosine as an oil which was identified by nmr spectroscope and used without further purification.

Workup

  1. customThis material was prepared
  2. temperaturewith cooling in an ice bath
  3. customThe resulting reaction mixture
  4. extractionafter which time it was extracted with three 250 ml portions of diethyl ether
  5. additionEthyl acetate (500 ml) was then added to the aqueous phase
  6. additionfollowed by the careful addition of 200 ml of concentrated hydrochloric acid
  7. customThe organic layer was separated
  8. washwashed with two 500 ml portions of water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customEvaporation of the solvent under reduced pressure
  11. customafter removal of the drying agent
  12. filtrationby filtration

Sources & evidence

ORD record
ord-9e25eed8c23b452b9d9888c34280aa95
Source dataset
uspto-grants-1981_02
Patent number
US04250086

Reaction notes

Loading…