Triethylamine → Benzyl 3-oxoazetidine-1-carboxylate

HRID 1506842Notes

Reaction equation

HRID 1506842 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 5 C). 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 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. dry with materialdried over sodium sulfate
  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-b48b4927ef9f43c8b67cfc12cd885c95
Source dataset
uspto-grants-2015_12
Patent number
US09221782B2

Reaction notes

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