HCID 69882101, compound → HCID 69881648, compound

HRID 397853Notes

Reaction equation

HRID 397853 reaction equation
[F:1][C:2]1[C:3]([F:45])=[CH:4][C:5]2[C:10]3[C:11]4[C:42](=[O:43])[NH:41][C:40](=[O:44])[C:12]=4[C:13]4[C:14]5[C:19]([N:20]([C@@H:22]6[O:35][C@@H:34]7[CH2:36][O:37][C@@H:32]([CH2:33]7)[C@H:23]6[O:24]CC6C=CC=CC=6)[C:21]=4[C:9]=3[NH:8][C:6]=2[CH:7]=1)=[CH:18][C:17]([F:38])=[C:16]([F:39])[CH:15]=5>[OH-].[OH-].[Pd+2].C1COCC1>[F:1][C:2]1[C:3]([F:45])=[CH:4][C:5]2[C:10]3[C:11]4[C:42](=[O:43])[NH:41][C:40](=[O:44])[C:12]=4[C:13]4[C:14]5[C:19]([N:20]([C@@H:22]6[O:35][C@@H:34]7[CH2:36][O:37][C@@H:32]([CH2:33]7)[C@H:23]6[OH:24])[C:21]=4[C:9]=3[NH:8][C:6]=2[CH:7]=1)=[CH:18][C:17]([F:38])=[C:16]([F:39])[CH:15]=5

Participants

4

Reactant 1

HCID 69882101HCID 69882101, compound

Product 1

HCID 69881648HCID 69881648, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,3,9,10-tetrafluoro-12-(2—O-benzyl-3, 6-anhydro-4-deoxy-β-D-glucopyranosyl)-6, 7, 12, 13-tetrahydro(5H)indolo[2, 3-a]pyrrolo[3, 4-c]carbazole-5, 7-dione (0.034 g, 0.055 mmol) and 20% Pd(OH)2/C (0.048 g) in 5 mL of freshly distilled THF was hydrogenated (balloon pressure) at room temperature for 5 days. The resulting mixture was filtered through a bed of Celite and the cake was washed with THF and then with methanol. The filtrate was evaporated and the residue was chromatographed (Sephadex LH-20/ methanol) to give the title compound (0.017 g, 59%) as a yellow solid: 1H NMR (THF-d8, 400 MHz) δ 11.15 (br s, 1H), 10.17 (br s, 1H), 9.19 (dd, J=11.1, 8.5 Hz, 1H), 9.09 (dd, J=11.2, 8.3 Hz, 1H), 7.81 (dd, J=11.6, 6.7 Hz, 1H), 7.51 (dd, 10.5, 6.7 Hz, 1H), 6.21 (d, J=7.3 Hz, 1H), 5.37 (br s, 1H), 4.89 (s, 1H), 4.57 (m, 2H), 4.27 (d, J=9.7 Hz, 1H), 3.85 (d, J=9.1 Hz, 1H), 3.09 (d, J=13.4 Hz, 1H), 2.09 (dd, J=13.1, 6.0 Hz, 1H); MS (ESI−) m/e 524 (M−H)−; HPLC: 99.0% (270 nm).

Workup

  1. customat room temperature
  2. customfor 5 days
  3. filtrationThe resulting mixture was filtered through a bed of Celite
  4. washthe cake was washed with THF
  5. customThe filtrate was evaporated
  6. customthe residue was chromatographed (Sephadex LH-20/ methanol)

Sources & evidence

ORD record
ord-1af54d6983cd420e930c6bb57f7dc1af
Source dataset
uspto-grants-2003_08
Patent number
US06610727B2

Reaction notes

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