Acetic Acid → HCID 69479057, compound

HRID 856312Notes

Reaction equation

HRID 856312 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:10]([CH:11]=1)[CH2:9][C@H:8]([CH2:12][N:13]1[CH2:18][CH2:17][N:16]([C:19](OC(C)(C)C)=O)[CH2:15][CH2:14]1)[O:7]2)([O-:3])=[O:2].FC(F)(F)C(O)=O.C(N(CC)CC)C.[C:40]1([C:46]2[CH:53]=[CH:52][C:49](C=O)=[CH:48][CH:47]=2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[B-]C#N.[Na+].C(O)(=O)C>C(Cl)Cl>[C:40]1([C:46]2[CH:47]=[CH:48][CH:49]=[CH:52][CH:53]=2)[CH:45]=[CH:44][C:43]([CH2:19][N:16]2[CH2:15][CH2:14][N:13]([CH2:12][C@@H:8]3[O:7][C:6]4=[N:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][N:10]4[CH2:9]3)[CH2:18][CH2:17]2)=[CH:42][CH:41]=1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 76689(1,1'-Biphenyl)-4-carboxaldehydeHCID 20587905Sodium cyanoborohydride [MI]HCID 69635301HCID 69635301, compound

Product 1

HCID 69479057HCID 69479057, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl (S)-4-(6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)piperazine-1-carboxylate prepared in Example 394 (7.2 g, 20.26 mmol), trifluoroacetic acid (24 ml) and methylene chloride (72 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methylene chloride (100 ml), then neutralized with triethylamine (20 ml, 143.49 mmol). The solution was concentrated under reduced pressure, and the residue was dissolved in methanol (72 ml). To the solution, 4-phenylbenzaldehyde (7.38 g, 40.52 mmol), sodium cyanotrihydroborate (3.82 g, 60.78 mmol), and acetic acid (3.48 ml, 60.78 mmol) were added in this order followed by stirring at room temperature for 24 hours. The precipitates were filtered off, washed with methanol, and purified by silica gel column chromatography (methylene chloride/methanol=10/1) to afford (S)-2-[4-(biphenyl-4-ylmethyl)piperazin-1-ylmethyl]-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (5.52 g, yield 65%) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in methylene chloride (100 ml)
  3. concentrationThe solution was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol (72 ml)
  5. stirringby stirring at room temperature for 24 hours
  6. filtrationThe precipitates were filtered off
  7. washwashed with methanol
  8. custompurified by silica gel column chromatography (methylene chloride/methanol=10/1)

Sources & evidence

ORD record
ord-9b8b13211f8e4867969b45ce57ffd009
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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