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

HRID 53116Notes

Reaction equation

HRID 53116 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 get, 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 get, 1:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-685e9e8f4e914f6b855025114d741b88
Source dataset
uspto-grants-1997_04
Patent number
US05618792

Reaction notes

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