Allyl chloroformate → (2R)-4-(methylsulfanyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}butanoic acid

HRID 1719467Notes

Reaction equation

HRID 1719467 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].Cl[C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12]>[OH-].[Na+]>[CH2:14]([O:13][C:11]([NH:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6])=[O:12])[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 18052Allyl chloroformateHCID 84815D-Methionine

Product 1

HCID 13491536(2R)-4-(methylsulfanyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}butanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 15.00 g D-methionine in 25.2 ml 4N sodium hydroxide cooled to about 0° C. is added, with stirring, 15.60 ml allyl chloroformate and 41.49 ml 4N sodium hydroxide. After the addition is completed, the reaction is stirred for an additional ten minutes at 0° C. and then allowed to warm to room temperature for an additional 20 minutes. The reaction mixture is then washed twice with ethyl ether. The aqueous layers are separated, acidified to pH2 with concentrated hydrochloric acid and then refrigerated for one hour. The cooled solution is then extracted three times with 100 ml portions of ethyl ether. The ether extracts are combined, dried over anhydrous sodium sulfate and the solvents removed under vacuum to afford the title product having

Workup

  1. additionis added
  2. additionAfter the addition
  3. stirringthe reaction is stirred for an additional ten minutes at 0° C.
  4. washThe reaction mixture is then washed twice with ethyl ether
  5. customThe aqueous layers are separated
  6. extractionThe cooled solution is then extracted three times with 100 ml portions of ethyl ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvents removed under vacuum

Sources & evidence

ORD record
ord-74c258d437ca43748c31026d47517f4e
Source dataset
uspto-grants-1985_09
Patent number
US04540580

Reaction notes

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