Methanol → HCID 66818415, compound

HRID 1755132Notes

Reaction equation

HRID 1755132 reaction equation
[C:1]([O:5][C:6](=[O:48])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:46][CH2:45][C:21]3([N:25]=[C:24]([C:26]4[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([O:36]CC5C=CC=CC=5)[CH:27]=4)[NH:23][C:22]3=[O:44])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:9]([CH3:47])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[H][H].ClCCl.CO>C(OCC)(=O)C.C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:48])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:19][CH2:20][C:21]3([N:25]=[C:24]([C:26]4[CH:31]=[C:30]([C:32]([F:33])([F:35])[F:34])[CH:29]=[C:28]([OH:36])[CH:27]=4)[NH:23][C:22]3=[O:44])[CH2:45][CH2:46]2)(=[O:16])=[O:17])=[C:9]([CH3:47])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 66817821HCID 66817821, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66818415HCID 66818415, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-{2-[2-(3-Benzyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester (952.0 mg, 1.39 mmol) was dissolved in ethyl acetate (15.0 ml)-THF (5.0 ml). Pd—C (190.4 mg) was added and the mixture was stirred at room temperature for one hour in a hydrogen atmosphere. After completion of the reaction, the precipitated solid was dissolved by adding dichloromethane and methanol, and the remaining black solid was then filtered off through celite. The filtrate was concentrated under reduced pressure to give 4-{2-[2-(3-hydroxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester as a white solid (776.2 mg, 93.8%).

Workup

  1. customAfter completion of the reaction
  2. dissolutionthe precipitated solid was dissolved
  3. filtrationthe remaining black solid was then filtered off through celite
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bf3c1bd256a344108e91401aa9e962fe
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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