Pyridine → HCID 545702, compound

HRID 1009200Notes

Reaction equation

HRID 1009200 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.C(=O)(O)[O-].[NH4+].[N:34]1C=CC=CC=1>C(#N)C.O>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]([C:11](=[O:13])[NH2:34])[CH3:10])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 85082Tert-butoxycarbonylalanineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 545702HCID 545702, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

DL-N-Boc-alanine (5.0 g, 26.4 mmol), di-tert-butylpyrocarbonate (7.9 mL, 34 mmol), and ammonium bicarbonate (2.5 g, 32 mmol) were stirred together in acetonitrile (101 mL). Pyridine (1.3 mL, 16 mmol) was added. The mixture stirred for 12 hours. Water was added and then the acetonitrile was removed in vacuo. The resulting slurry was filtered. The solid was collected, dissolved in methylene chloride and methanol (90:10), dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound (2.7 g, 55%): 1H NMR (400 MHz, d6-DMSO): 7.20 (br s, 1H), 6.90 (br s, 1H), 6.77 (d, 1H), 3.86 (quintet, 1H), 1.37 (s, 9H), 1.15 (d, 3H).

Workup

  1. customthe acetonitrile was removed in vacuo
  2. filtrationThe resulting slurry was filtered
  3. customThe solid was collected
  4. dissolutiondissolved in methylene chloride
  5. dry with materialmethanol (90:10), dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ac756e1f275145d1ad279116997f2f00
Source dataset
uspto-grants-2011_07
Patent number
US07973061B2

Reaction notes

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