Pyridine → 3-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile

HRID 1636887Notes

Reaction equation

HRID 1636887 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:17]([CH3:19])[CH3:18])[CH:13]([OH:16])[C:14]#[N:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](OC(=O)C)(=[O:28])[CH3:27]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:17]([CH3:19])[CH3:18])[CH:13]([O:16][C:26](=[O:28])[CH3:27])[C:14]#[N:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 151604623-[(Benzyloxycarbonyl)amino]-2-hydroxy-4-methylpentanenitrile

Product 1

HCID 228716173-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrileYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution containing 3-[(benzyloxycarbonyl)amino]-2-hydroxy-4-methylpentanenitrile (32.0 g, 0.12 mol) and pyridine (59 mL) was added acetic anhydride (73.6 g, 68 mL, 0.72 mol) dropwise at RT. After 3 h the reaction was diluted with ethyl acetate and washed with water. The organic layer was separated, dried (anhydrous magnesium sulfate) and evaporated. The residue was purified by column chromatography (silica gel, 1:1 hexane:ethyl acetate) to give 33.08 g (94.0%) of 3-(S)-[(benzyloxycarbonyl)amino]-2-acetoxy-4-methylpentanenitrile as a viscous yellow oil; TLC Rf =0.70 (silica gel, 1:1 hexane:ethyl acetate).

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated
  5. customThe residue was purified by column chromatography (silica gel, 1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-bc2455e2d1594d97a0a1426800014a40
Source dataset
uspto-grants-2000_03
Patent number
US06037325

Reaction notes

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