Benzyl chloroformate → N,N'-Dicarbobenzyloxy-L-ornithine

HRID 1657910Notes

Reaction equation

HRID 1657910 reaction equation
Cl.[NH2:2][C@@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH2:6][NH2:7].[OH-:11].[Na+].[C:13](Cl)([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>>[C:13]([NH:2][C@@H:3]([C:8]([OH:10])=[O:9])[CH2:4][CH2:5][CH2:6][NH:7][C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:11])([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 443122D-Ornithine monohydrochloride

Product 1

HCID 7073472N,N'-Dicarbobenzyloxy-L-ornithine

Procedure

A solution of D-ornithine monohydrochloride in 60 ml. of 2N sodium hydroxide was cooled to 5°C. Carbobenzoxy chloride (20.4 g.) and 2N sodium hydroxide (64 ml.) were added in four equal portions over 1.0 hour with stirring. The mixture was stirred for an additional 0.5 hour in the cold, then extracted with diethyl ether. The aqueous portion was chilled and acidified (25 ml. 6N hydrochloric acid) and the resulting oil was extracted into ether containing some ethyl acetate. The organic phase was extracted with water, then saturated salt solution and dried (MgSO4). Evaporation of the solvent gave an oil which crystallized from ether to afford 18.8 gms. of product, m.p. 110.5°-113°C.

Workup

  1. stirringThe mixture was stirred for an additional 0.5 hour in the cold,
  2. extractionthen extracted with diethyl ether
  3. temperatureThe aqueous portion was chilled
  4. extractionthe resulting oil was extracted into ether containing some ethyl acetate
  5. extractionThe organic phase was extracted with water
  6. dry with materialsaturated salt solution and dried (MgSO4)
  7. customEvaporation of the solvent
  8. customgave an oil which
  9. customcrystallized from ether
  10. customto afford 18.8 gms

Sources & evidence

ORD record
ord-e1d534b4998340e094c6d9ad131e114e
Source dataset
uspto-grants-1976_06
Patent number
US03962317

Reaction notes

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