1,4-Dioxane → 6-Azido-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-norleucine

HRID 1779968Notes

Reaction equation

HRID 1779968 reaction equation
[C:1]([O-:4])([OH:3])=O.[Na+].[CH:6]1[C:18]2[CH:17](OC(Cl)=O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.[NH2:23][C@@H:24]([CH2:28][CH2:29][CH2:30][CH2:31][N:32]=[N+:33]=[N-:34])[C:25]([OH:27])=[O:26].OS([O-])(=O)=O.[K+].O1CCOC[CH2:42]1>>[CH:8]1[C:9]2[CH:17]([CH2:42][O:3][C:1]([NH:23][C@@H:24]([CH2:28][CH2:29][CH2:30][CH2:31][N:32]=[N+:33]=[N-:34])[C:25]([OH:27])=[O:26])=[O:4])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:18]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 15764092HCID 15764092, compoundHCID 16666241159610-92-1

Product 1

HCID 251460636-Azido-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-L-norleucine

Procedure

11.6 ml 1N NaHCO3 solution (11.6 mmol) and a solution of 3.00 g 9-fluorenyloxycarbonylchloride (11.6 mmol) in 12 ml dioxane were added to the crude solution of (S)-2-amino-6-azidohexanoic acid (7.73 mmol) and stirring under argon was continued overnight. The solution was acidified to pH 2 by addition of a KHSO4 -solution, extracted with ethyl acetate, dried (MgSO4), and the residue was purified by flash chromatography (hexane/ethyl acetate/acetic acid 7/3/0.5).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. customthe residue was purified by flash chromatography (hexane/ethyl acetate/acetic acid 7/3/0.5)

Sources & evidence

ORD record
ord-707abd42ec5344709e39a3db95f9aafb
Source dataset
uspto-grants-1997_05
Patent number
US05629293

Reaction notes

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