Triethylamine → HCID 86749052, compound

HRID 2210710Notes

Reaction equation

HRID 2210710 reaction equation
[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@@H:10]1[C@@H:13]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[C:15]2=[O:30])[NH:12][C:11]1=[O:31])[CH3:9])=[O:6])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:39]([O:42][C:43](=[O:47])[C:44](Cl)=[O:45])[CH:40]=[CH2:41]>ClCCl.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([O:7][C@@H:8]([C@@H:10]1[C@@H:13]([C@@H:14]2[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][CH2:21][O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:24])[CH3:25])[C:15]2=[O:30])[N:12]([C:44](=[O:45])[C:43]([O:42][CH2:39][CH:40]=[CH2:41])=[O:47])[C:11]1=[O:31])[CH3:9])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 3018516Allyl chlorooxoacetateHCID 57297599HCID 57297599, compound

Product 1

HCID 86749052HCID 86749052, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

In dichloromethane (2.5 ml) was dissolved the (3S,4R)-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-4-[(1S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-2-oxocyclohexan-1-yl]azetidin-2-one (0.56 g) obtained in Reference Example 3 and while the solution was stirred, a solution of triethylamine (0.7 ml) in dichloromethane (2.5 ml) was added. Then, a solution of allyloxyoxalyl chloride (0.55 g) in dichloromethane (2.5 ml) was added dropwise at -78° C. over a period of 10 minutes. The reaction mixture was stirred at -78° C. for 5 minutes and, then, at 0° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, washed with phosphate buffer (pH 7) and aqueous sodium chloride in that order and, after addition of triethylamine (0.2 ml), dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (stationary phase: silica gel 15 g; ethyl acetate-hexane 1:6) to give allyl [(3S,4R)-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-4-[(1S)-3-[2-(tert-butyldimethylsilyloxy)ethyl]-2-oxocyclohexan-1-yl]-2-oxoazetidin-1-yl]glyoxylate.

Workup

  1. customobtained in Reference Example 3 and while the solution
  2. stirringThe reaction mixture was stirred at -78° C. for 5 minutes
  3. washwashed with phosphate buffer (pH 7) and aqueous sodium chloride in that order
  4. additionafter addition of triethylamine (0.2 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by flash column chromatography (stationary phase: silica gel 15 g; ethyl acetate-hexane 1:6)

Sources & evidence

ORD record
ord-81fbeabf6e5c4f468a468660eea6fe20
Source dataset
uspto-grants-1995_10
Patent number
US05459260

Reaction notes

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