Sodium Bicarbonate → HCID 178495693, compound

HRID 1509726Notes

Reaction equation

HRID 1509726 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[NH:20][C:19]2[C:21]3[C:26]([CH:27]=[CH:28][C:18]=2[N:17]=1)=[CH:25][C:24]1[C:29]2[C:34]([CH2:35][O:36][C:23]=1[CH:22]=3)=[CH:33][C:32]([C:37]1[NH:41][C:40]([C@@H:42]3[CH2:46][C@H:45]([CH2:47][O:48][CH3:49])[CH2:44][N:43]3[C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])=[N:39][CH:38]=1)=[CH:31][CH:30]=2)=O)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>C(O)C.[Pd]>[CH3:49][O:48][CH2:47][C@@H:45]1[CH2:44][N:43]([C:50]([O:52][C:53]([CH3:56])([CH3:54])[CH3:55])=[O:51])[C@H:42]([C:40]2[NH:41][C:37]([C:32]3[CH:33]=[C:34]4[CH2:35][O:36][C:23]5[CH:22]=[C:21]6[C:26]([CH:27]=[CH:28][C:18]7[N:17]=[C:16]([C@@H:12]8[CH2:13][CH2:14][CH2:15][NH:11]8)[NH:20][C:19]=76)=[CH:25][C:24]=5[C:29]4=[CH:30][CH:31]=3)=[CH:38][N:39]=2)[CH2:46]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 178495692HCID 178495692, compound

Product 1

HCID 178495693HCID 178495693, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (2S,4S)-2-[5-(2-{(2S)-1-[(benzyloxy)carbonyl]pyrrolidin-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 (724 mg, 0.96 mmol) and 70 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, 454 mg. Purification by reverse phase HPLC gave 65 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-a77fcd4991b14a759e70a4001ae6ccf0
Source dataset
uspto-grants-2015_12
Patent number
US09221833B2

Reaction notes

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