Benzyl chloroformate → Nalphabenzyloxycarbonyl-DL-methionine amide

HRID 2270884Notes

Reaction equation

HRID 2270884 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][CH:13]([C:18]([NH2:20])=[O:19])[CH2:14][CH2:15][S:16][CH3:17].[OH-].[Na+].CC(OC)(C)C>O>[CH2:1]([O:8][C:9]([NH:12][CH:13]([C:18]([NH2:20])=[O:19])[CH2:14][CH2:15][S:16][CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 5687422-Amino-4-(methylthio)butanamide

Product 1

HCID 3359717Nalphabenzyloxycarbonyl-DL-methionine amideYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

51 ml benzyloxycarbonyl chloride was dripped into a solution of 50 g (0.34 mole) DL-methionine amide in 200 ml water at 5-20° C., during which the pH was maintained at 7-9 with sodium hydroxide solution. A slimy precipitate formed immediately which became finely crystalline upon the addition of 200 ml MTBE. After the end of the addition the mixture was agitated 30 min further at room temperature. The precipitated, colorless crystals were then filtered off, washed with a little MTBE and recrystallized out of 700 ml toluene. After filtering off, washing with toluene and drying, 67 g (69%) Nαbenzyloxycarbonyl-DL-methionine amide with a melting point of 120-122° C. was obtained.

Workup

  1. customA slimy precipitate formed immediately which
  2. additionAfter the end of the addition the mixture
  3. filtrationThe precipitated, colorless crystals were then filtered off
  4. washwashed with a little MTBE
  5. customrecrystallized out of 700 ml toluene
  6. filtrationAfter filtering off
  7. washwashing with toluene
  8. customdrying

Sources & evidence

ORD record
ord-7f17bed410f1416485389579c640c7c4
Source dataset
uspto-grants-2001_12
Patent number
US06333176B1

Reaction notes

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