Hydrochloric Acid → HCID 15035397, compound

HRID 1090280Notes

Reaction equation

HRID 1090280 reaction equation
C[O:2][C:3](=[O:38])[C:4]([CH3:37])([CH3:36])[CH2:5][C:6]1[N:7](C2C=CC([N+]([O-])=O)=CC=2)[C:8]2[C:13]([C:14]=1[S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:17])=[O:16])=[CH:12][C:11]([CH:24]([CH3:26])[CH3:25])=[CH:10][CH:9]=2.[OH-].[Na+].Cl>C(OCC)(=O)C.CO.C1COCC1.[Pd]>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:24][N:7]2[C:8]3[C:13](=[CH:12][C:11]([CH:24]([CH3:26])[CH3:25])=[CH:10][CH:9]=3)[C:14]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[C:6]2[CH2:5][C:4]([CH3:36])([CH3:37])[C:3]([OH:2])=[O:38])=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54109298HCID 54109298, compound

Product 1

HCID 15035397HCID 15035397, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 480 mg methyl[1-(4-nitrophenyl)-α,α-dimethyl-5-isopropyl -3-phenylsulfonylindole-2-propanoate] in 45 ml ethyl acetate was heated with 100 mg Pd/C (5%) catalyst and the solution hydrogenated a 45 psi for 16 h. A further 50 mg catalyst was added and the hydrogenation continued for another 16 h. The catalyst was removed by filtration through celite and the product isolated (480 mg) after removal of solvent. Hydrolysis was achieved by treatment of the ester with 2N NaOH in 3 ml MeOH/THF 1:1. The solution was neutralized with 0.5N HCl and the product extracted with ethyl acetate 3×10 ml. The solution was dried (Na2SO4) and stripped to yield the title product, m.p. 290° decomposition.

Workup

  1. customfor 16 h
  2. customThe catalyst was removed by filtration through celite
  3. customthe product isolated (480 mg)
  4. customafter removal of solvent
  5. customHydrolysis
  6. extractionthe product extracted with ethyl acetate 3×10 ml
  7. dry with materialThe solution was dried (Na2SO4)

Sources & evidence

ORD record
ord-3503e5c146324ab5b11449dfea1b509d
Source dataset
uspto-grants-1992_01
Patent number
US05081138

Reaction notes

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