Pyridine → 3-(s)-[(Benzyloxycarbonyl)amino]-2-(r,s)-acetoxy-4-methyl pentanoic acid

HRID 2393252Notes

Reaction equation

HRID 2393252 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:18]([CH3:20])[CH3:19])[CH:13]([OH:17])[C:14]([OH:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:18]([CH3:20])[CH3:19])[CH:13]([O:17][C:27](=[O:29])[CH3:28])[C:14]([OH:16])=[O: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 131720810HCID 131720810, compound

Product 1

HCID 1317208113-(s)-[(Benzyloxycarbonyl)amino]-2-(r,s)-acetoxy-4-methyl pentanoic acidYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(S)-[(benzyloxycarbonyl)amino]-2-(R,S)-hydroxy-4-methylpentanoic acid (1.70 g, 6.04 mmol) and pyridine (4.9 mL) was added acetic anhydride (5.7 mL, 6.17 g, 60.4 mmol) dropwise at room temperature. The reaction was allowed to stir overnight and was diluted with ethyl acetate and washed with water (2×). The organic layer was dried over magnesium sulfate, filtered and evaporated in vacuo to give a thick oil. The residue was purified by column chromatography on silica gel with 15% methanol/dichloromethane to afford 1.56 g (80%) of 3-(S)-[(benzyloxycarbonyl)amino]-2-(R,S)-acetoxy-4-methyl pentanoic acid as a light yellow viscous oil. FAB MS [M+H] m/z; Calcd: 324, Found: 324.

Workup

  1. washwashed with water (2×)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customto give a thick oil
  6. customThe residue was purified by column chromatography on silica gel with 15% methanol/dichloromethane

Sources & evidence

ORD record
ord-946e513d28cc44a79d8514d6b131907c
Source dataset
uspto-grants-1998_09
Patent number
US05807829

Reaction notes

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