Trifluoroacetic acid → HCID 86747648, compound

HRID 486773Notes

Reaction equation

HRID 486773 reaction equation
C(OC([N:8]1[CH2:40][C@@H:39]2[C@@H:10]([CH2:11][C:12]3[N:13]([CH2:38]2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=2[C:20]=3[C:21]2[C:22](=[O:37])[O:23][C:24](=[O:36])[C:25]=2[C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[N:28]([CH3:35])[CH:27]=2)[CH2:9]1)=O)(C)(C)C.[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44]>ClCCl>[F:41][C:42]([F:47])([F:46])[C:43]([OH:45])=[O:44].[CH2:9]1[C@@H:10]2[CH2:11][C:12]3[N:13]([CH2:38][C@@H:39]2[CH2:40][NH:8]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=1[C:20]=3[C:21]1[C:22](=[O:37])[O:23][C:24](=[O:36])[C:25]=1[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]([CH3:35])[CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86747647HCID 86747647, compound

Product 1

HCID 86747648HCID 86747648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 5 g of cis-3-[2-(tertbutoxycarbonyl)-2,3,3a,4,11,11a-hexahydro-1H-pyrrolo[3',4':4,5]-pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione [prepared as described in Example 5(viii)] in 200 ml of dichloromethane was treated with 30 ml of trifluoroacetic acid. After 0.5 hour the solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel using dichloromethane/methanol/acetic acid/water (90:18:3:2) for the elution. Removal of the solvent gave 4.5 g of cis-3-[2,3,3a,4,11, 11a-hexahydro-1H-pyrrolo[3',4':4,5]pyrido[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)furan-2,5-dione trifluoroacetate of melting point 199°-201° C.

Workup

  1. customAfter 0.5 hour the solvent was removed under reduced pressure
  2. customthe residue was purified by chromatography on silica gel
  3. washfor the elution
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-7ae7297ccfa342b7a06c65229f9bcc22
Source dataset
uspto-grants-1994_03
Patent number
US05292747

Reaction notes

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