Acetic Anhydride → 5-[4'-(Acetylhydrazinocarbonyl)-2'-methylbiphenyl-4-carbonyl]-1'-ethyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

HRID 1741126Notes

Reaction equation

HRID 1741126 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]2([C:19]3[C:11](=[CH:12][C:13]4[CH2:14][CH2:15][N:16]([C:20]([C:22]5[CH:27]=[CH:26][C:25]([C:28]6[CH:33]=[CH:32][C:31]([C:34]([NH:36][NH2:37])=[O:35])=[CH:30][C:29]=6[CH3:38])=[CH:24][CH:23]=5)=[O:21])[C:17]=4[CH:18]=3)[O:10][CH2:9]2)[CH2:5][CH2:4]1)[CH3:2].[C:39](OC(=O)C)(=[O:41])[CH3:40]>C(Cl)(Cl)Cl>[C:39]([NH:37][NH:36][C:34]([C:31]1[CH:32]=[CH:33][C:28]([C:25]2[CH:24]=[CH:23][C:22]([C:20]([N:16]3[C:17]4[CH:18]=[C:19]5[C:6]6([CH2:9][O:10][C:11]5=[CH:12][C:13]=4[CH2:14][CH2:15]3)[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]6)=[O:21])=[CH:27][CH:26]=2)=[C:29]([CH3:38])[CH:30]=1)=[O:35])(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 218337121'-Ethyl-5-(4'-hydrazinocarbonyl-2'-methylbiphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]

Product 1

HCID 539730445-[4'-(Acetylhydrazinocarbonyl)-2'-methylbiphenyl-4-carbonyl]-1'-ethyl-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine]Yield 2,623.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1'-ethyl-5-(4'-hydrazinocarbonyl-2'-methylbiphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E61, 1.00 g, 1.96 mmole) in chloroform (30 ml), acetic anhydride (5.76 ml, 0.06 mmole) was slowly added. The solution was stirred at room temperature for approximately 1 hour, then concentrated in vacuo. Toluene was used to azeotrope out the excess acetic anhydride. The residue was dissolved in chloroform, washed with 10% Na2CO3 solution and the organic phase dried (Na2SO4), then concentrated in vacuo. The residue beige solid was chromatographed on silica gel, eluting with 0-12% methanol in chloroform to afford the title compound as a yellow solid (0.87 g, 80%) m.p. 154-157° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with 10% Na2CO3 solution
  4. dry with materialthe organic phase dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue beige solid was chromatographed on silica gel
  7. washeluting with 0-12% methanol in chloroform

Sources & evidence

ORD record
ord-8356d05c2f65441b80e1347feca9ab0f
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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