Ethanethiol → HCID 86596561, compound

HRID 1715792Notes

Reaction equation

HRID 1715792 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]([C:14](O)=O)[CH2:4][S:3]1.C1(N=C=N[CH:26]2[CH2:31]CCCC2)CCCCC1.C([SH:34])C>C(#N)C.CN(C)C1C=CN=CC=1>[CH2:31]([C:14]([C@@H:5]1[CH2:4][S:3][C:2](=[O:1])[N:6]1[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[S:34])[CH3:26]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 10868DicyclohexylcarbodiimideHCID 11470406HCID 11470406, compound

Product 1

HCID 86596561HCID 86596561, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

In 200 ml of acetonitrile was dissolved 10 g of (4R)-2-oxo-3-benzylthiazolidin-4-carboxylic acid, and 9.2 g of dicyclohexylcarbodiimide was added to the solution under room temperature. Subsequently, to the solution were added 3.3 ml of ethanethiol, and 670 mg of 4-dimethylaminopyridine in this order under ice-cooling, and the mixture was stirred at room temperature for 2 hours. Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=10:1) to give 10.8 g of (4S)-4-ethylthiocarbonyl-3-benzylthiazolidin-2-one as oily product.

Workup

  1. additionwas added to the solution under room temperature
  2. temperaturecooling
  3. filtrationInsoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-7d020ddb8abf4c04ab2c8b761ad034f4
Source dataset
uspto-grants-2010_09
Patent number
US07799929B2

Reaction notes

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