Chloroacetone → HCID 14856645, compound

HRID 1655622Notes

Reaction equation

HRID 1655622 reaction equation
[CH2:1]([N:8]1[CH:12]([CH2:13][SH:14])[CH:11]([OH:15])[N:10]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:25][C:26](=[O:28])[CH3:27]>C1COCC1>[CH2:1]([N:8]1[CH:12]([CH2:13][S:14][CH2:25][C:26](=[O:28])[CH3:27])[CH:11]([OH:15])[N:10]([CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:9]1=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 14856644HCID 14856644, compound

Product 1

HCID 14856645HCID 14856645, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1.85 g (5.63 mmol) of (4 RS, 5 R) 1,3-dibenzyl-2-oxo-5-mercaptomethylimidazolidin-4-ol (prepared according to Example 2) and 7.0 ml of THF is treated at 0°-5° C. with 0.855 g (1.18 ml, 8.45 mmol) of TEA and 0.547 g (0.47 ml, 5.91 mmol) of chloroacetone. The mixture is stirred at 0° C. for 2 hours and then at room temperature for 2 hours. The precipitate is filtered off and the solvent is removed by distillation. After flash chromatography, 1.956 g (90% of theory) of (4 RS, 5 R)-1,3-dibenzyl-2-oxo-5-(4-oxo-2-thiapentyl)imidazolidin-4-ol, Rf =0.24 (EtOAc/hexane 3:2) are obtained.

Workup

  1. waitat room temperature for 2 hours
  2. filtrationThe precipitate is filtered off
  3. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-403b5ad7034046b8bf812eb141f1b669
Source dataset
uspto-grants-1993_10
Patent number
US05250699

Reaction notes

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