Benzyl chloroformate → HCID 13146030, compound

HRID 256331Notes

Reaction equation

HRID 256331 reaction equation
[CH2:1]([NH:3][C@@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].O1CCOCC1.[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>[OH-].[Na+].O>[CH2:21]([O:28][C:29]([N:3]([CH2:1][CH3:2])[C@@H:4]([C:12]([OH:14])=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 312751,4-DioxaneHCID 13049157HCID 13049157, compound

Product 1

HCID 13146030HCID 13146030, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

2.9 g (0.015 mole) of N-ethyl-D-phenylalanine (Example 3, Step A) are dissolved in 22.5 ml of 2N sodium hydroxide, 10 ml of dioxane are added, the mixture is cooled to 5° to 10° C., then 2.5 ml (about 0.017 mole) of benzyloxycarbonyl chloride are added and the reaction mixture is stirred for 3 hours at cooling. Subsequently it is diluted with 40 ml of water and extracted with 30 ml of a mixture of diethyl ether-petroleum ether-1:1, when a three-phase system is formed. The two lower phases are again extracted with 30 ml of diethyl ether, then the combined diethyl ether layers are washed with 20 ml of water. The aqueous layers are combined and acidified with N sulfuric acid to pH 2. The separated product is extracted three times with 30 ml of ethyl acetate. The ethyl acetate layers are combined, washed twice with 20 ml of water, dried over anhydrous sodium sulfate and evaporated on a water bath having a temperature of max. 40° C. at 15 to 20 millibars. Yield 2.7 g (55%) of an oil.

Workup

  1. temperaturethe mixture is cooled to 5° to 10° C.
  2. temperatureat cooling
  3. extractionextracted with 30 ml of a mixture of diethyl ether-petroleum ether-1:1, when a three-phase system
  4. customis formed
  5. extractionThe two lower phases are again extracted with 30 ml of diethyl ether
  6. washthe combined diethyl ether layers are washed with 20 ml of water
  7. extractionThe separated product is extracted three times with 30 ml of ethyl acetate
  8. washwashed twice with 20 ml of water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated on a water bath
  11. custom40° C.

Sources & evidence

ORD record
ord-1de0db5cc22b4bcc869143944dc25c65
Source dataset
uspto-grants-1987_10
Patent number
US04703036

Reaction notes

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