Pyridine → HCID 10565709, compound

HRID 2258601Notes

Reaction equation

HRID 2258601 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][NH2:18])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:17][NH:18][C:25](=[O:27])[CH3:26])[C:13]([O:15][CH3:16])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 110432213-Amino-N-((phenylmethoxy)carbonyl)-L-alanine methyl ester

Product 1

HCID 10565709HCID 10565709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2(S)-benzyloxycarbonylamino-3-aminopropionate (2.5 g) in methylene chloride was added pyridine (20 mL) and acetic anhydride (5 mL). After stirring for 2 h the solution was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate and concentrated in vacuo. Upon evaporation pyridine hydrochloride precipitated and was removed by filtration. The filtrate was evaporated to obtain the title compound. 1H NMR (300 MHz, CDCl3) δ 7.28 (5H, s), 6.14 (1H, s), 5.97 (1H, d), 5.10 (2H, s), 4.41 (1H, m), 3.78 (3H, s), 1.93 (3H, s).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionThe ethyl acetate layer was extracted w/50 mL each of 2% potassium hydrogen sulfate, saturated sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customUpon evaporation pyridine hydrochloride
  7. customprecipitated
  8. customwas removed by filtration
  9. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-74d3482bd5434429beb5f6bd68ffd2e0
Source dataset
uspto-grants-1997_08
Patent number
US05661161

Reaction notes

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