Perchloric Acid → methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate

HRID 1473189Notes

Reaction equation

HRID 1473189 reaction equation
[CH2:1]([N:8]1[C:12]2[C:13](=[O:31])[N:14]([CH3:30])[C:15]([CH:24]([OH:29])[C:25]([O:27][CH3:28])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]2[C:13](=[O:31])[N:14]([CH3:30])[C:15]([CH:24]([O:29][C:2]([CH3:7])([CH3:3])[CH3:1])[C:25]([O:27][CH3:28])=[O:26])=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)[C:11]=2[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 89462710methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate

Product 1

HCID 89462902methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetateYield 206.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10908tert-Butyl acetateSolvent

Procedure

A solution of methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-hydroxyacetate (3.3 g, 4.53 mmol) in t-Butyl acetate (30 mL) was treated with perchloric acid (0.423 mL, 7.04 mmol) and the resultant was stirred at room temperature for 3 hours. The mixture was diluted with Ethyl acetate, washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel (0-70% ethyl acetate/hexanes) to afford methyl 2-(1-benzyl-4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetate (2.3 g, 4.67 mmol, 73% yield) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.43-7.47 (m, 3H) 7.37-7.41 (m, 1H) 7.32-7.35 (m, 4H) 7.01-7.05 (m, 1H) 5.92-5.96 (m, 1H) 5.83-5.88 (m, 2H) 5.21-5.24 (m, 1H) 3.82 (s, 3H) 3.67 (s, 3H) 0.96 (s, 9H); LCMS (m/z) ES+=493 (M+1).

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c7344de523274fef91a649ae2a095007
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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