Acetaldehyde → (1S)-1-Methylthiocarbonyloxyethyl-2-methylpropanoate

HRID 558063Notes

Reaction equation

HRID 558063 reaction equation
[O-]Cl.[Na+].CS.C(=O)C.[CH3:9][CH:10]([CH3:22])[C:11]([O:13][CH:14]([O:18][C:19]([CH3:21])=[S:20])[CH:15](C)C)=[O:12]>P([O-])([O-])([O-])=O>[CH3:21][C:19]([O:18][C@H:14]([O:13][C:11](=[O:12])[CH:10]([CH3:22])[CH3:9])[CH3:15])=[S:20]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 878MethanethiolHCID 23665760Sodium HypochloriteHCID 866102712-Methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate

Product 1

HCID 86633037(1S)-1-Methylthiocarbonyloxyethyl-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Procedure

A 20-L, multi-necked, cylindrical reactor, fitted with a mechanical stirrer, a nitrogen inlet and an outlet connected to an oxidation bath, and a bleach bath (14% NaOCl) to oxidize librated methanethiol and acetaldehyde is charged with racemic 2-methyl-1-methylthiocarbonyloxypropyl 2-methylpropanoate (2b) (5.32 kg, 25.8 mol) and 0.8 M phosphate buffer (10 L, pH 7.0). Solid supported Candida antarctica lipase A (125 g, NOVOZYME® 735, NOVOZYME®; CHIRAZYME™ L-5, Roche Diagnostics; or other suppliers) is slowly added while stirred. The reaction mixture is stirred at room temperature (22-24° C.) for ca. 18 hours.

Workup

  1. customconnected to an oxidation bath, and a bleach bath
  2. additionis slowly added
  3. stirringThe reaction mixture is stirred at room temperature (22-24° C.) for ca. 18 hours

Sources & evidence

ORD record
ord-3525701c7a124f948883bc250d388855
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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