Triethylamine → allyl (4R)-2-diazo-4-[(2R,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidine-2-yl]-3-oxopentanoate

HRID 620796Notes

Reaction equation

HRID 620796 reaction equation
[Si:1]([O:8][C@@H:9]([C@H:11]1[C:14](=[O:15])[NH:13][C@@H:12]1[C@@H:16]([CH3:26])[C:17](=[O:25])[CH2:18][C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.C1(C)C=CC(S([N:43]=[N+:44]=[N-])(=O)=O)=CC=1>C(#N)C>[N+:43](=[C:18]([C:17](=[O:25])[C@@H:16]([C@@H:12]1[C@@H:11]([C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[CH3:10])[C:14](=[O:15])[NH:13]1)[CH3:26])[C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])=[N-:44]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 14138755(3S,4R)-3-[(R)-1-t-butyldimethylsilyloxyethyl]-4-[(R)-1-methyl-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

Product 1

HCID 131715918allyl (4R)-2-diazo-4-[(2R,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidine-2-yl]-3-oxopentanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of allyl (4R)-4-[(2R,3S)-3-{(1R)-1-t-butyldimethylsilyloxyethyl}-4-oxoazetidin-2-yl]-3-oxopentanoate (6.52 g) and triethylamine (6.8 ml) in acetonitrile (50 ml) was added a lM solution (17 ml) of p-toluenesulfonyl azide in acetonitrile at 0°-5° C. and the mixture was stirred at the same temprature for 2 hours. The mixture was concentrated under reduced pressure to give a residue. The residue was triturated with hexane. The precipitates were filtered off. The filtrate was concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (80 g) and eluted with a mixture of ethyl acetate and hexane (1:9 V/V) to give allyl (4R)-2-diazo-4-[(2R,3S)-3{(1R)-1-t-butyldimetylsilyloxyethyl}-4-oxoazetidin-2-yl]-3-oxopentanoate (3.78 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customto give a residue
  3. customThe residue was triturated with hexane
  4. filtrationThe precipitates were filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with a mixture of ethyl acetate and hexane (1:9 V/V)

Sources & evidence

ORD record
ord-0bffb1d339de48c9aed8fe3a8516795a
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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