Ethanol → HCID 54315569, compound

HRID 275603Notes

Reaction equation

HRID 275603 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH2:5][NH:6][C:7]([C:9]([S:12]([CH2:15][CH:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])([CH3:11])[CH3:10])=[O:8].O.[CH2:28](O)[CH3:29]>>[OH:3][CH2:4][CH2:5][NH:6][C:7]([C:9]([S:12]([CH2:15][C@H:16]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:17]([O:19][CH2:28][CH3:29])=[O:18])(=[O:14])=[O:13])([CH3:10])[CH3:11])=[O:8]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14798Sodium HydroxideHCID 53939121HCID 53939121, compound

Product 1

HCID 54315569HCID 54315569, compound

Procedure

0.1N sodium hydroxide solution was added dropwise while stirring to a mixture of 0.86 g (2.23 mmol) of rac-α-[[[1-[(2 -hydroxyethyl)carbamoyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamic acid and 200 mg of α-chymotrypsin in 5 ml of ethanol and 100 ml of water in such a manner that the pH value was held at 7.5. After sodium hydroxide solution was no longer consumed the working-up of the reaction mixture was effected by adjusting to pH 8 and extracting twice with 40 ml of ether each time. The combined organic extracts were washed with 15 ml of saturated sodium hydrogen carbonate solution, dried over sodium sulphate and evaporated under reduced pressure. There was obtained ethyl (R)-α-[[[1-[(2-hydroxyethyl)carbamoyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate as a yellowish oil.

Workup

  1. customAfter sodium hydroxide solution was no longer consumed the
  2. extractionextracting twice with 40 ml of ether each time
  3. washThe combined organic extracts were washed with 15 ml of saturated sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3bf9a1b73062438d80a29cbb6e51ca5d
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

Loading…