Acetic Acid → HCID 68952121, compound

HRID 1432526Notes

Reaction equation

HRID 1432526 reaction equation
C([O:4][CH:5]1[CH:10]=[CH:9][CH2:8][N:7]([C:11](=[O:24])[C@@H:12]([CH:21]([CH3:23])[CH3:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:6]1)(=O)C.[OH-].[Na+].C(O)(=O)C.C(Cl)(Cl)Cl>CCO>[C:14]([NH:13][C@@H:12]([C:11]([N:7]1[CH2:8][CH:9]=[CH:10][CH:5]([OH:4])[CH2:6]1)=[O:24])[CH:21]([CH3:23])[CH3:22])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 68947314HCID 68947314, compound

Product 1

HCID 68952121HCID 68952121, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.254 g of 3-acetoxy-N—(N-BOC-(R)-valyl)-1,2,3,6-tetrahydropyridine, dissolved in 5 ml of EtOH are treated with 2N ethanolic NaOH under ice-cooling. To the mixture obtained acetic acid is added in order to neutralize the reaction mixture and solvent is evaporated. The evaporation residue obtained is mixed with CHCl3, the mixture obtained is washed with NaCl-solution, the organic phase is dried and solvent is evaporated. N—(N-BOC-(R)-valyl)-1,2,3,6-tetrahydropyridin-3-ol is obtained. 1H-NMR: 5.9(m,2H,HIV, HV), 4.51, 4.45(2xdd,1H, NHCHCO,J=5.2 Hz,J=9.0 Hz), 1.4 (b,9H,(CH3)3), 0.9(m,6H,CH(CH3)2).

Workup

  1. temperaturecooling
  2. additionis added in order
  3. customis evaporated
  4. customThe evaporation residue obtained
  5. customthe mixture obtained
  6. washis washed with NaCl-solution
  7. customthe organic phase is dried
  8. customsolvent is evaporated

Sources & evidence

ORD record
ord-9398f0d220b2492ba3b7b716e38ab877
Source dataset
uspto-grants-2009_11
Patent number
US07612103B2

Reaction notes

Loading…