L-Tartaric acid → HCID 68611995, compound

HRID 2095380Notes

Reaction equation

HRID 2095380 reaction equation
C(OC([N:11]1[CH2:14][CH2:13][C@H:12]1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:28][CH:27]3[CH:25]([CH2:26]3)[CH2:24]2)[CH:20]=[N:21][CH:22]=1)=O)C1C=CC=CC=1.[C:29]([OH:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CO.[Pd]>[C:34]([C@@H:32]([C@H:30]([C:29]([OH:38])=[O:37])[OH:31])[OH:33])([OH:36])=[O:35].[NH:11]1[CH2:14][CH2:13][C@H:12]1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([N:23]2[CH2:24][CH:25]3[CH:27]([CH2:26]3)[CH2:28]2)[CH:20]=[N:21][CH:22]=1

Participants

5

Reactant 2

HCID 444305L-Tartaric acidHCID 59371389HCID 59371389, compound

Product 1

HCID 68611995HCID 68611995, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-[5-[[1-(benzyloxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]-3-azabicyclo[3.1.0]hexane (395 mg, 1.04 mmol) in methanol (30 mL) in a 100 mL round-bottom flask were added L-tartaric acid (156 mg, 1.04 mmol) and 10% palladium on carbon (40 mg). The atmosphere was exchanged with H2 (3 times), and the mixture was stirred under H2 (1 bar) for 3 h. The mixture was filtered through a cotton plug, and the filtrate was concentrated. The residue was further dried with an oil pump at room temperature to give the product as a brittle, tan foam (404 mg, 91%). Anal. Calcd. for C14H19N3.O1.09C6H4O6.1.06H2O (FW 428.0): C, 51.52; H, 6.51; N, 9.82. Found: C, 51.61; H, 6.60; N, 9.72.

Workup

  1. filtrationThe mixture was filtered through a cotton plug
  2. concentrationthe filtrate was concentrated
  3. customThe residue was further dried with an oil pump at room temperature

Sources & evidence

ORD record
ord-69f9e96e79124792a28999e52f57f455
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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