Ammonium formate → HCID 69655001, compound

HRID 1061429Notes

Reaction equation

HRID 1061429 reaction equation
C([O-])=O.[NH4+].[C:5]([N:8]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH2:21][CH:20]([N:22](CC3C=CC=CC=3)[CH2:23][C@H:24]([OH:41])[CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([O:33]CC4C=CC=CC=4)=[CH:29][CH:28]=3)[CH2:19]2)=[CH:14][CH:13]=1)[C:9](=[O:11])[CH3:10])(=[O:7])[CH3:6]>CO.[Pd]>[C:5]([N:8]([C:12]1[CH:13]=[CH:14][C:15]([N:18]2[CH2:19][CH:20]([NH:22][CH2:23][C@H:24]([OH:41])[CH2:25][O:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)[CH2:21]2)=[CH:16][CH:17]=1)[C:9](=[O:11])[CH3:10])(=[O:7])[CH3:6]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69654990HCID 69654990, compound

Product 1

HCID 69655001HCID 69655001, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ammonium formate (0.57 g, 9.1 mmol) was added to a solution of N-acetyl-N-[4-(3-{benzyl-[(2S)-3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-amino}-azetidin-1-yl)-phenyl]-acetamide (which was obtained in Example 402) (0.25 g, 0.45 mmol) and 10% Pd/C (0.05 g) in dry methanol (7 mL). The reaction was stirred at room temperature overnight. The solution was passed through a pad of celite and then was concentrated. The crude solid was treated with saturated aqueous NaHCO3 (30 mL) followed by extraction with ethyl acetate (3×20 mL). The organic extract was dried over anhydrous sodium sulfate, filtered, and evaporated to afford 0.18 g of the desired product as a white solid; 1H NMR (300 MHz, CDCl3) δ 2.05 (s, 6H), 2.61 (s, 1H), 2.75 (m, 2H), 3.49 (m, 2H), 3.75 (m, 1H), 3.85 (d, 2H, J=7.13 Hz), 4.02 (t, 2H, J=5.3 Hz), 4.12 (q, 1H), 6.32 (d, 2H, J=11.12 Hz), 6.90 (d, 2H, J=11.32 Hz), 6.55 (q, 4H, J=4.6 Hz), 7.53 (d, 2H, J=7.02 Hz), 7.61 (brs, 1H); MS (ES) m/z: 414.0 (MH+).

Workup

  1. concentrationwas concentrated
  2. additionThe crude solid was treated with saturated aqueous NaHCO3 (30 mL)
  3. extractionfollowed by extraction with ethyl acetate (3×20 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-358edc4034a348ada2a04b3f313b9d60
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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