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

HRID 363740Notes

Reaction equation

HRID 363740 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-methylpentanenitrile

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-18454674b49e4d469a7627c4c3db9bb5
Source dataset
uspto-grants-1999_02
Patent number
US05874585

Reaction notes

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