HCID 89590814, compound → HCID 117598893, compound

HRID 522380Notes

Reaction equation

HRID 522380 reaction equation
[CH:1]1([C@H:6]2[C:35](=[O:36])[N:34]3[CH2:37][C@@H:31]([CH2:32][C@H:33]3[C:38]([O:40][CH3:41])=[O:39])[O:30][C:18]3=[N:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]([O:27][CH2:28][CH3:29])=[C:17]3[CH2:16][CH:15]=[CH:14][CH2:13][CH2:12][C@@H:11]3[CH2:42][CH2:43][CH2:44][C@H:10]3[O:9][C:8](=[O:45])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.CO.[Rh]>[CH:1]1([C@H:6]2[C:35](=[O:36])[N:34]3[CH2:37][C@@H:31]([CH2:32][C@H:33]3[C:38]([O:40][CH3:41])=[O:39])[O:30][C:18]3=[N:19][C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=4[C:26]([O:27][CH2:28][CH3:29])=[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]3[CH2:42][CH2:43][CH2:44][C@H:10]3[O:9][C:8](=[O:45])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 1

HCID 89590814HCID 89590814, compound

Product 1

HCID 117598893HCID 117598893, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 23948RhodiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (3aR,7S,10S,12R,21E,24aS)-7-cyclopentyl-19-ethoxy-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 (Example 1, Step 4) (100 mg) in ethyl acetate (20 ml) and methanol (20 ml) was added 5% Rh/C (20 mg) and the mixture was stirred for 18 hours under hydrogen atmosphere. After exchanging the atmosphere for nitrogen, the reaction mixture was filtered and concentrated to give the desired product as a foam (100 mg). LRMS (ES+) M/Z (M+H)+ 622.1.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b197706a18e54170a717505fb6df986e
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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