Methanol → 3[8(S)-[1(S)-tert.butoxyformamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-1H-pyrrole-2,5-dione

HRID 863548Notes

Reaction equation

HRID 863548 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:13]1[CH2:47][CH2:46][N:16]2[C:17]3[C:22]([C:23]([C:24]4C(=O)OC(=O)[C:28]=4[C:29]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH:30]=4)=[C:15]2[CH2:14]1)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)N[Si](C)(C)C.C[OH:58].C[N:60]([CH3:63])[CH:61]=[O:62]>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:13]1[CH2:47][CH2:46][N:16]2[C:17]3[C:22]([C:23]([C:24]4[C:63](=[O:58])[NH:60][C:61](=[O:62])[C:28]=4[C:29]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH:30]=4)=[C:15]2[CH2:14]1)=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 6228DimethylformamideHCID 13838Hexamethyldisilazane2×HCID 867521493[8(S)-[1(S)-tert.butoxy formamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-furan-2,5-dione

Product 1

HCID 675886783[8(S)-[1(S)-tert.butoxyformamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-1H-pyrrole-2,5-dione

Conditions

Temperature
50 °C

Procedure

A solution of 1.6 g (2.54 mmol) of 3[8(S)-[1(S)-tert.butoxy formamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-furan-2,5-dione in 20 ml of dry N,N-dimethylformamide was treated with 5.35 ml (25.4 mmol) of hexamethyldisilazane and 0.41 g (12.8 mmol) of methanol. The solution was heated at 50° C. for 3 hours and then treated with an additional 5.35 ml (24.8 mmol) of hexamethyldisilazane and 0.41 g (12.8 mmol) of methanol. After a total of 6 hours the solvent was evaporated under reduced pressure and the residue was re-evaporated with 20 ml of methanol. Flash chromatography of the residue on silica gel using ethyl acetate/hexane (1:2) for the elution gave 1.35 g of 3[8(S)-[1(S)-tert.butoxyformamido-2-methylpropyl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(1-phenyl-3-indolyl)-1H-pyrrole-2,5-dione as a red solid of melting point 165°-168° C.

Workup

  1. customAfter a total of 6 hours the solvent was evaporated under reduced pressure
  2. customthe residue was re-evaporated with 20 ml of methanol
  3. washfor the elution

Sources & evidence

ORD record
ord-6281280e6fce478fac5b48813bc8db2b
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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