Acetic Anhydride → HCID 67924983, compound

HRID 973947Notes

Reaction equation

HRID 973947 reaction equation
Cl.Cl.[CH3:3][NH:4][C@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].C(N(CC)CC)C>O1CCCC1>[CH3:3][N:4]([C:16](=[O:18])[CH3:17])[C@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 131717082HCID 131717082, compound

Product 1

HCID 67924983HCID 67924983, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl-3-(4-pyridinyl)alanine, dihydrochloride (1.4 g, 0.0053 mol) is stirred in dry tetrahydrofuran (20 mL) with acetic anhydride (0.9 mL, 0.0095 mol) and triethylamine (3.3 mL, 0.0233 mol) at room temperature. After stirring at room temperature overnight the mixture is diluted with 20 mL tetrahydrofuran and filtered and the solids washed with tetrahydrofuran. The filtrate is concentrated to a dark oil, dissolved in dichloromethane (50 mL) and washed with dilute sodium bicarbonate solution (50 mL). The organic layer is dried over magnesium sulfate and concentrated. The residue is triturated with diethyl ether, filtered, and dried to afford 0.83 g of the title compound as a tan solid; mp 86-88° C.

Workup

  1. filtrationfiltered
  2. washthe solids washed with tetrahydrofuran
  3. concentrationThe filtrate is concentrated to a dark oil
  4. dissolutiondissolved in dichloromethane (50 mL)
  5. washwashed with dilute sodium bicarbonate solution (50 mL)
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue is triturated with diethyl ether
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-c8d965055175402d9e915464d654c559
Source dataset
uspto-grants-1991_11
Patent number
US05066662

Reaction notes

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