Ethanethiol → HCID 86596561, compound

HRID 2057129Notes

Reaction equation

HRID 2057129 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-d69cdcd809f44e02a24b6273812ae565
Source dataset
uspto-grants-2008_02
Patent number
US07335778B2

Reaction notes

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