HCID 66817849, compound → HCID 66815936, compound

HRID 1754943Notes

Reaction equation

HRID 1754943 reaction equation
[CH:1]1([C:7]2[NH:11][C:10](=[O:12])[C:9]3([CH2:17][CH2:16][N:15]([S:18](/[CH:21]=[CH:22]/[C:23]4[C:31]5[O:30][C:29](=[O:32])[NH:28][C:27]=5[CH:26]=[CH:25][CH:24]=4)(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CO.CN(C=O)C.[Pd]>[CH:1]1([C:7]2[NH:11][C:10](=[O:12])[C:9]3([CH2:17][CH2:16][N:15]([S:18]([CH2:21][CH2:22][C:23]4[C:31]5[O:30][C:29](=[O:32])[NH:28][C:27]=5[CH:26]=[CH:25][CH:24]=4)(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 66817849HCID 66817849, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66815936HCID 66815936, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Procedure

10% Pd—C (28 mg) was added to a solution of 2-cyclohexyl-8-[(E)-2-(2-oxo-2,3-dihydro-benzoxazol-7-yl)-ethenesulfonyl]-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (56.6 mg, 0.123 mmol) in MeOH-DMF (4 ml, 1:1). The mixture was stirred at room temperature overnight in a hydrogen atmosphere. The reaction mixture was filtered through celite, and the filtrate was then concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate, and the organic layer was then washed with water (×2), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, AcOEt-hexane) to give 2-cyclohexyl-8-[2-(2-oxo-2,3-dihydro-benzoxazol-7-yl)-ethanesulfonyl]-1,3,8-triaza-spiro[4.5]dec-1-en-4-one as a colorless foam (46.9 mg, 83%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. additionThe resulting residue was diluted with ethyl acetate
  4. washthe organic layer was then washed with water (×2)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel, AcOEt-hexane)

Sources & evidence

ORD record
ord-4826b515dd224137a38dcdb53347fd4a
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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