HCID 178470407, compound → HCID 178420975, compound

HRID 1675911Notes

Reaction equation

HRID 1675911 reaction equation
C([O:3][C:4]([C:6]1[NH:33][N:32]=[C:31]2[C:7]=1[CH2:8][CH:9]1[CH:22]3[CH:13]([C:14]4[CH:15]=[CH:16][C:17]([O:23]CC5C=CC=CC=5)=[CH:18][C:19]=4[CH2:20][CH2:21]3)[CH2:12][CH2:11][C:10]12[CH3:34])=[O:5])C>[Pd].C1COCC1.C(O)C>[OH:23][C:17]1[CH:16]=[CH:15][C:14]2[CH:13]3[CH:22]([CH2:21][CH2:20][C:19]=2[CH:18]=1)[CH:9]1[CH2:8][C:7]2[C:31]([C:10]1([CH3:34])[CH2:11][CH2:12]3)=[N:32][NH:33][C:6]=2[C:4]([OH:5])=[O:3]

Participants

5

Reactant 1

HCID 178470407HCID 178470407, compound

Product 1

HCID 178420975HCID 178420975, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on charcoal (50 mg, 5% Pd) was added to a solution 2-Benzyloxy-6a-methyl-4b,5,6,6a,8,10,10a,10b,11,12-decahydro-7,8-diaza-pentaleno[2,1-a]phenanthrene-9-carboxylic acid ethyl ester(214 mg, 0.5 mmol, CAB03051) in THF (15 mL) and ethanol (15 mL). The resulting mixture was stirred under a hydrogen-atmosphere (balloon) for 24 hours, filtered through a 3 cm layer of celite and concentrated under reduced pressure. The residue was dried under high vacuum. Yield: 165 mg (98%) light grey solid. 1H-NMR (DMSO-d6, 400 MHz), δ: 0.92 (s, 3H, —CH3), 1.30-2.86 (m, 13H), 6.44 (d, J=2.3 Hz, 1H), 6.52 (dd, J=8.6, 2.3 Hz, 1H), 7.05 (d, J=8.6 Hz, 1H), 9.02 (s, 1H, —OH), 12.90 (bs, 2H, —COOH and NH). LRMS (FAB+): 176.0 (100), 329.1 (45, [M+H]+). HRMS (FAB+): 339.171135 C20H23N2O3requires 339.170868

Workup

  1. filtrationfiltered through a 3 cm layer of celite and
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-2b13e4038f39496e893b598292b85358
Source dataset
uspto-grants-2011_08
Patent number
US08003783B2

Reaction notes

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