Water → HCID 86751631, compound

HRID 2294683Notes

Reaction equation

HRID 2294683 reaction equation
[OH-].[Ca+2].[OH-].[CH2:4]([O:6][C:7]([CH:9]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][S:11]([C:14]([CH3:25])([CH3:24])[CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])(=[O:13])=[O:12])=[O:8])[CH3:5].O>C(O)C>[C:19]([O:18][C:17]([NH:16][CH2:15][C:14]([S:11]([CH2:10][C@H:9]([CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:7]([O:6][CH2:4][CH3:5])=[O:8])(=[O:12])=[O:13])([CH3:25])[CH3:24])=[O:23])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 6093208Calcium HydroxideHCID 86751630HCID 86751630, compound

Product 1

HCID 86751631HCID 86751631, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 0.039N calcium hydroxide solution is added while stirring to a mixture of 1.75 g (4.1 mmol) of tert-butyl [2-[[(RS)-2-(ethoxycarbonyl)-3-phenylpropyl]sulphonyl]-2-methylpropyl]carbamate and 70 mg of α-chymotrypsin in 5 ml of ethanol and 250 ml of water in such a manner that the pH value is maintained at 7.5. When calcium hydroxide is no longer consumed, the working-up of the reaction mixture is effected by extracting the aqueous solution twice with 50 ml of ethyl acetate each time. The combined organic phases are washed with 25 ml of saturated sodium bicarbonate solution, dried over sodium sulphate and evaporated under reduced pressure. There is obtained 0.86 g of ethyl (R)-α-[[[2-(1-tert-butoxyformamido)-1,1-dimethylethyl]sulphonyl]methyl]hydrocinnamate as a yellowish oil; MS: 445 (M+NH4)+.

Workup

  1. customWhen calcium hydroxide is no longer consumed
  2. extractionby extracting the aqueous solution twice with 50 ml of ethyl acetate each time
  3. washThe combined organic phases are washed with 25 ml of saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a7e3827f30fb493c845754784f9c9e83
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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