HCID 117598889, compound → HCID 178421216, compound

HRID 522381Notes

Reaction equation

HRID 522381 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[CH2:47][N:23]([C:24](=[O:46])[C@H:25]([CH:41]4[CH2:45][CH2:44][CH2:43][CH2:42]4)[NH:26][C:27](=[O:40])[O:28][C@:29]4([CH3:39])[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:48]([OH:50])=[O:49])[CH2:21]3)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH:41]1([C@H:25]2[C:24](=[O:46])[N:23]3[CH2:47][C@@H:20]([CH2:21][C@H:22]3[C:48]([OH:50])=[O:49])[O:19][C:11]3=[N:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:9]([OH:8])=[C:10]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C@@H:30]3[CH2:36][CH2:37][CH2:38][C@@:29]3([CH3:39])[O:28][C:27](=[O:40])[NH:26]2)[CH2:42][CH2:43][CH2:44][CH2:45]1

Participants

4

Reactant 1

HCID 117598889HCID 117598889, compound

Product 1

HCID 178421216HCID 178421216, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3aR,7S,10S,12R,21E,24aS)-19-(benzyloxy)-7-cyclopentyl-3a-methyl-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-carboxylic acid (synthesized as described in Example 1 with intermediates B7 and C3) (113 mg) in ethyl acetate (5 ml) was added 10% Pd/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 (93 mg). LRMS (ES+) M/Z (M+H)+ 594.7.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-324a012dbd374f0ea7fef47c3d0c3a86
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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