Sodium Bicarbonate → HCID 178495689, compound

HRID 1509730Notes

Reaction equation

HRID 1509730 reaction equation
C(OC([N:11]1[C@@H:15]([CH3:16])[CH2:14][CH2:13][C@H:12]1[C:17]1[NH:21][C:20]2[C:22]3[C:27]([CH:28]=[CH:29][C:19]=2[N:18]=1)=[CH:26][C:25]1[C:30]2[C:35]([CH2:36][O:37][C:24]=1[CH:23]=3)=[CH:34][C:33]([C:38]1[NH:42][C:41]([C@@H:43]3[CH2:47][C@H:46]([CH2:48][O:49][CH3:50])[CH2:45][N:44]3[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[N:40][CH:39]=1)=[CH:32][CH:31]=2)=O)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)C.[Pd]>[CH3:50][O:49][CH2:48][C@@H:46]1[CH2:45][N:44]([C:51]([O:53][C:54]([CH3:56])([CH3:55])[CH3:57])=[O:52])[C@H:43]([C:41]2[NH:42][C:38]([C:33]3[CH:34]=[C:35]4[CH2:36][O:37][C:24]5[CH:23]=[C:22]6[C:27]([CH:28]=[CH:29][C:19]7[N:18]=[C:17]([C@@H:12]8[CH2:13][CH2:14][C@H:15]([CH3:16])[NH:11]8)[NH:21][C:20]=76)=[CH:26][C:25]=5[C:30]4=[CH:31][CH:32]=3)=[CH:39][N:40]=2)[CH2:47]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 178495688tert-butyl(2S,4S)-2-[5-(2-{(2S,5S)-1-[(benzyloxy)carbonyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate

Product 1

HCID 178495689HCID 178495689, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (2S,4S)-2-[5-(2-{(2S,5S)-1-[(benzyloxy)carbonyl]-5-methylpyrrolidin-2-yl}-1,11-dihydroisochromeno[4′,3′:6,7]naphtho[1,2-d]imidazol-9-yl)-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidine-1-carboxylate (830 mg, 1.08 mmol) and 100 mg 10% Pd/C in 20 mL ethanol was hydrogenated at 1 atm overnight. Additional 10% Pd/C (300 mg) and a portion of solid NaHCO3 was added and hydrogenation continued for 4 hours. Filtration through celite and concentration of the filtrate under reduced pressure gave the product as a dark brown solid, 722 mg. Purification by reverse phase HPLC gave 100 mg purified product.

Workup

  1. customwas hydrogenated at 1 atm overnight
  2. filtrationFiltration through celite and concentration of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-c3fc137dcce942ac9b890d035c6a3eb0
Source dataset
uspto-grants-2015_12
Patent number
US09221833B2

Reaction notes

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