HCID 117598824, compound → HCID 178501305, compound

HRID 522391Notes

Reaction equation

HRID 522391 reaction equation
C([O:8][C:9]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:12]=[C:11]2[O:19][C@H:20]3[CH2:45][N:23]([C:24](=[O:44])[C@H:25]([C:40]([CH3:43])([CH3:42])[CH3:41])[NH:26][C:27](=[O:39])[O:28][C@@H:29]4[CH2:38][CH2:37][CH2:36][C@H:30]4[CH2:31][CH2:32][CH:33]=[CH:34][CH2:35][C:10]=12)[C@H:22]([C:46]([O:48][CH3:49])=[O:47])[CH2:21]3)C1C=CC=CC=1>C1COCC1.CO.[Pd]>[C:40]([C@H:25]1[C:24](=[O:44])[N:23]2[CH2:45][C@@H:20]([CH2:21][C@H:22]2[C:46]([O:48][CH3:49])=[O:47])[O:19][C:11]2=[N:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:9]([OH:8])=[C:10]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]2[CH2:36][CH2:37][CH2:38][C@H:29]2[O:28][C:27](=[O:39])[NH:26]1)([CH3:43])([CH3:41])[CH3:42]

Participants

5

Reactant 1

HCID 117598824HCID 117598824, compound

Product 1

HCID 178501305HCID 178501305, compoundYield 87.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (3aR,7S,10S,12R,21E,24aS)-19-(benzyloxy)-7-tert-butyl-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,23,24,24a-tetradecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxylate (synthesized as in Example 1 with intermediates B6 and C3) (1.16 g) in THF (8.7 ml) and methanol (8.7 mL) was added 10% Pd/C (92 mg) and the mixture was stirred for 18 hours under hydrogen atmosphere. The atmosphere was changed to nitrogen and the reaction was carefully filtered through celite to give 0.88 g of the desired product. LRMS (ES+) m/z 582.40 (M+H)+.

Workup

  1. filtrationthe reaction was carefully filtered through celite

Sources & evidence

ORD record
ord-f9619b517f9b4e919d4ec22b80393cb8
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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