Acetone → 4-Isopropyl-6-(benzyloxycarbonylmethoxy)-2-phenylthiomethylsaccharin

HRID 129046Notes

Reaction equation

HRID 129046 reaction equation
[CH:1]([C:4]1[CH:14]=[C:13]([OH:15])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].[C:25]([O-:28])([O-])=[O:26].[K+].[K+].[CH2:31](C(Br)C([O-])=O)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[CH3:43]C(C)=O>>[CH:1]([C:4]1[CH:14]=[C:13]([O:15][CH2:43][C:25]([O:28][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:26])[CH:12]=[C:11]2[C:5]=1[C:6](=[O:24])[N:7]([CH2:16][S:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 103166544-Isopropyl-6-hydroxy-2-phenylthiomethylsaccharinHCID 21881508Benzylbromoacetate

Product 1

HCID 699595434-Isopropyl-6-(benzyloxycarbonylmethoxy)-2-phenylthiomethylsaccharin

Procedure

A mixture of 4-isopropyl-6-hydroxy-2-phenylthiomethyl-saccharin (3.5 g, 9.63 mmol), acetone (25 mL) and K2CO3 (2.66 g, 19.26 mmol) was stirred under nitrogen for 2 minutes, then benzylbromoacetate (2.4 mL, 14.45 mmol) was added. The mixture was stirred for 6 hours, filtered, and the filtrate was concentrated in vacuo. The residue was purified by medium pressure chromatography eluting with 20% ethyl acetate/hexane to afford 4.67 (100%) of 4-isopropyl-6-(benzyloxycarbonylmethoxy)-2-phenylthiomethylsaccharin.

Workup

  1. stirringThe mixture was stirred for 6 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by medium pressure chromatography
  5. washeluting with 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e9f3eb7da128481f975bd89182c9bd1c
Source dataset
uspto-grants-1995_11
Patent number
US05466701

Reaction notes

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