Sulfuric Acid → HCID 53915581, compound

HRID 1855922Notes

Reaction equation

HRID 1855922 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[O-2].[Mg+2].Cl[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)=[O:13].S(=O)(=O)(O)O>O.CCOCC>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:12]([N:1]2[CH2:8][CH2:7][CH2:6][C@H:2]2[C:3]([OH:5])=[O:4])=[O:13])=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 70304p-Tolyl chloroformateHCID 145742L-ProlineHCID 6850729Magnesium monoxide

Product 1

HCID 53915581HCID 53915581, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

In this example, 11.5 g L-proline and 8.0 g magnesium oxide are dissolved in 100 ml water, and then admixed with 60 ml ether. A solution of p-methylphenyl chloroformate [8.5 g; boiling point: 109°-110° C. (28-30 mmHg)] dissolved in 50 ml ether is added thereto, while cooling the mixture in an ice bath (5°-10° C.). After stirring for 30 minutes, the reaction solution is acidified by adding 60 ml concentrated sulfuric acid, and extracted three times with 60 ml ethyl acetate. The extract is washed three times with 40 ml 2N HCl and four times with 50 ml water, and then dried overnight over anhydrous sodium sulfate (30 g). After drying, the extract is filtered, and the filtrate is concentrated under reduced pressure. The resulting oily materials are admixed with 100 ml n-hexane, and left standing in a refrigerator (about -15° C.). The deposited crystals are filtered, and recrystallized from ethyl acetate-n-hexane (1:1 by volume), whereby p-methylphenyloxycarbonyl-L-proline (compound number 8; 9.25 g; mp: 76°-77° C.) is obtained. Yield: 74.3%.

Workup

  1. additionis added
  2. temperaturewhile cooling the mixture in an ice bath (5°-10° C.)
  3. extractionextracted three times with 60 ml ethyl acetate
  4. washThe extract is washed three times with 40 ml 2N HCl and four times with 50 ml water
  5. dry with materialdried overnight over anhydrous sodium sulfate (30 g)
  6. customAfter drying
  7. filtrationthe extract is filtered
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. waitleft
  10. customstanding in a refrigerator (about -15° C.)
  11. filtrationThe deposited crystals are filtered
  12. customrecrystallized from ethyl acetate-n-hexane (1:1 by volume)

Sources & evidence

ORD record
ord-aaff0358244345c58ebf1faff2e52c69
Source dataset
uspto-grants-1980_08
Patent number
US04217130

Reaction notes

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