Triethylamine → Benzyl 3-oxoazetidine-1-carboxylate

HRID 1027865Notes

Reaction equation

HRID 1027865 reaction equation
[OH:1][CH:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.S(=O)(=O)=O.N1C=CC=CC=1.C(N(CC)CC)C>CS(C)=O>[O:1]=[C:2]1[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 10081755Benzyl 3-hydroxyazetidine-1-carboxylate

Product 1

HCID 10632047Benzyl 3-oxoazetidine-1-carboxylateYield 101%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of the sub-title product of step (i) (17.9 g) in DMSO (100 mL) was added dropwise over 15 minutes to a solution of pyridine sulphur trioxide (44.7 g) and triethylamine (39.3 mL) in DMSO (200 ml) at 0° C. (slight exotherm to 5C). The mixture was warmed to RT after 5 minutes and stirred for 16 hours. The mixture was poured into ice/water and extracted twice with ethyl acetate. The combined organics were washed with brine, dried over is sodium sulfate and concentrated in vacuo to give crude product. The crude product was purified by flash silica chromatography, elution 100% dichloromethane. Pure fractions were evaporated to dryness to afford the sub-title product (17.9 g) as a pale yellow oil.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organics were washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give crude product
  6. customThe crude product was purified by flash silica chromatography, elution 100% dichloromethane
  7. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-428bfa32b10d42a3a68a3a0606f74674
Source dataset
uspto-grants-2014_05
Patent number
US08735413B2

Reaction notes

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