HCID 178431656, compound → HCID 178431655, compound

HRID 339857Notes

Reaction equation

HRID 339857 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:15]2[C:20]([CH3:22])([CH3:21])[O:19][C:18]([NH:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)=[N:17][S:16]2(=[O:31])=[O:30])[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[CH:24]1([NH:23][C:18]2[O:19][C:20]([CH3:22])([CH3:21])[CH:15]([C:11]3[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=3)[S:16](=[O:31])(=[O:30])[N:17]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 1

HCID 178431656HCID 178431656, compound

Product 1

HCID 178431655HCID 178431655, compoundYield 24.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

Under inert gas, 548 mg of [5-(3-benzyloxyphenyl)-6,6-dimethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-2-yl]cyclohexylamine were initially charged in 20 ml of methanol and, with addition of 263 mg of 10% Pd/C, stirred under a hydrogen atmosphere for 3.5 hours. The completeness of the conversion was checked by LCMS, and the reaction was once again admixed with 263 mg of 10% Pd/C and stirred under a hydrogen atmosphere for 2 days. After filtration to remove the solid residues, the filtrate was freed of the solvent under reduced pressure and dried under high vacuum. A portion (105 mg) of the residue thus obtained (468 mg) was purified in a purification laboratory by means of preparative HPLC, and the product-containing fractions were freed of the organic solvent under reduced pressure. The aqueous residue was lyophilized. This gave the product (66 mg) with a molecular weight of 352.4 g/mol (C17H24N2O4S); MS (ESI): m/e=353 (M+H+).

Workup

  1. stirringstirred under a hydrogen atmosphere for 2 days
  2. filtrationAfter filtration
  3. customto remove the solid residues
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-ab60f039972a4193b17f3c6826c173bf
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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