HCID 22612468, compound → HCID 22612485, compound

HRID 1857367Notes

Reaction equation

HRID 1857367 reaction equation
[CH2:1]([O:8][NH:9][C:10](=[O:33])[CH2:11][N:12]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15])C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:1][O:8][NH:9][C:10](=[O:33])[CH2:11][N:12]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=1)(=[O:24])=[O:23])[CH2:13][C:14]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15]

Participants

5

Reactant 2

HCID 22612468HCID 22612468, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22612485HCID 22612485, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxy-[(4-methoxybenzenesulfonyl)(2-morpholin-4-yl-2-oxoethyl)amino]acetamide (0.33 grams, 0.69 mmol) in methanol (35 mL) was added 5% palladium on activated carbon (85 mg). The mixture was agitated under 2 atmospheres hydrogen in a Parr shaker for 1.5 hours. The catalyst was removed by filtration through nylon (pore size 0.45 μm) and the solvent was evaporated. The residue was chromatorgraphed on silica gel with 5% methanol in methylene chloride to afford N-methoxy-[(4-methoxybenzenesulfonyl)(2-morpholin-4-yl-2-oxoethyl)amino]acetamide as a white solid, 65 mg (24%); 1H NMR (CD3OD): δ7.82 (d, J=9.0 Hz, 2H), 7.08 (d, J=9.0 Hz, 2H), 4.24 (s, 2H), 3.88 (s, 3H), 3.84 (s, 2H), 3.68-3.64 (m, 4H), 3.58-3.50 (m, 4H); MS (thermospray): m/z 388 (M+1), 387 (M); HRMS calculated for C16H22N3O7S (M+H): 388.1178, Found 338.1180.

Workup

  1. customThe catalyst was removed by filtration through nylon (pore size 0.45 μm)
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d7d7cce7fa134d2295929931913de720
Source dataset
uspto-grants-2000_11
Patent number
US06147074

Reaction notes

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