Ammonium formate → 4-Ethoxy-7-(t-butoxycarbonylmethoxy)saccharin ammonium salt

HRID 266483Notes

Reaction equation

HRID 266483 reaction equation
C([N:8]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([O:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:14]=[CH:15][C:16]=2[O:20][CH2:21][CH3:22])[S:9]1(=[O:11])=[O:10])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[NH4+:8].[CH2:21]([O:20][C:16]1[CH:15]=[CH:14][C:13]([O:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[C:12]2[C:17]=1[C:18](=[O:19])[NH:8][S:9]2(=[O:11])=[O:10])[CH3:22]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70052398HCID 70052398, compound

Product 1

HCID 867471344-Ethoxy-7-(t-butoxycarbonylmethoxy)saccharin ammonium saltYield 209.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

By the method of part D of Example 45 in two successive preparations 2-benzyl-4-ethoxy-7-(t-butoxycarbonylmethoxy) saccharin (0.5 g, 6.5 g) was debenzylated with ammonium formate (0.25 g, 3.66 g) and palladium on carbon (10%, 0.25 g, 2 g) in methanol affording 4-ethoxy-7-(t-butoxycarbonylmethoxy)saccharin ammonium salt (0.44 g, 5.63 g), phenylthiomethylation of which with chloromethyl phenyl sulfide (0.2 g, 2.38 g) in dimethylformamide and purification of the combined products (0.46 g, 6.42 g) by column chromatography on silica gel using dichloromethane and dichloromethane-acetone (98:2) as eluants afforded 2-phenylthiomethyl-4-ethoxy-7-(t-butoxycarbonylmethoxy)saccharin, 1.92 g, 40% yield.

Sources & evidence

ORD record
ord-6211423580fa423b88be6aefdcc439b5
Source dataset
uspto-grants-1997_07
Patent number
US05650422

Reaction notes

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