Ethanol → HCID 20499913, compound

HRID 652278Notes

Reaction equation

HRID 652278 reaction equation
[CH3:1][C:2]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])=[O:3].C(O)C.C(OCC(O)COC1C=CC([NH:27][C:28](=[O:32])[CH2:29][CH2:30]Cl)=CC=1)C>[OH-].[Na+]>[C:2]([NH:4][CH:5]([C:8]([OH:10])=[O:9])[CH2:6][S:7][CH2:30][CH2:29][C:28]([NH2:27])=[O:32])(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 702EthanolHCID 12035N-Acetyl-L-CysteineHCID 13884869HCID 13884869, compound

Product 1

HCID 20499913HCID 20499913, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A 1.63 g quantity of L-acetylcysteine was dissolved in 0.80 g of sodium hydroxide and 50 ml of a 70% aqueous solution of ethanol with ice cooling. To the solution was added 3.02 g of N-[4-(3-ethoxy-2-hydroxypropoxy)phenyl]-3-chloropropionamide. The mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated and the residue was adjusted to a pH of 3 with diluted hydrochloric acid, washed with chloroform and extracted with ethyl acetate. The ethyl acetate layer was dewatered with Glauber's salt and was concentrated. The residue was purified with acetone-ether, giving 3.95 g of N-] 4-(3-ethoxy-2-hydroxypropoxy)phenyl]-3-(2-acetylamino-2 carboxyethylthio)propionamide in a yield of 92.1 %. ##STR5##

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with chloroform
  3. extractionextracted with ethyl acetate
  4. concentrationwas concentrated
  5. customThe residue was purified with acetone-ether

Sources & evidence

ORD record
ord-ffec5a991a984e5ca6d426583ba57b5f
Source dataset
uspto-grants-1987_06
Patent number
US04670583

Reaction notes

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