HCID 11116749, compound → HCID 54131180, compound

HRID 279815Notes

Reaction equation

HRID 279815 reaction equation
[CH3:1][C:2]([CH3:13])([O:4][C:5]([NH:7][C@H:8]1[CH2:11][NH:10][C:9]1=[O:12])=[O:6])[CH3:3].C([Li])(CC)C.[CH3:19][S:20]([N:23]=[C:24]=[O:25])(=[O:22])=[O:21]>O1CCCC1.C1CCCCC1>[CH3:3][C:2]([CH3:13])([O:4][C:5]([NH:7][C@H:8]1[CH2:11][N:10]([C:24]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])=[O:25])[C:9]1=[O:12])=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 11116749HCID 11116749, compoundHCID 12668338Methanesulfonyl isocyanateHCID 178418400CID 53628100

Product 1

HCID 54131180HCID 54131180, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8078CyclohexaneSolvent

Conditions

Temperature
-75 °C

Procedure

(S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]-2-azetidinone (1.12 g) was dissolved in dry tetrahydrofuran (120 ml) and stirred at -75° C. under dry nitrogen. sec-Butyl lithium (4.44 ml of a 1.35 M solution in cyclohexane) was added and followed in two minutes by methylsulfonyl isocyanate (0.72 ml). After stirring for 25 minutes at -75° C., the reaction was quenched by the addition of 0.5 M pH 5.5 monobasic potassium phosphate buffer (60 ml), diluted with ethyl acetate-water, acidified to pH 2.5 with 3N hydrochloric acid, and (60 ml), diluted with ethyl acetate-water, acidified to pH 2.5 with 3N hydrochloric acid, and extracted with ethyl acetate (three times). The extract was washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness in vacuo to yield the desired product as a foam (1.73 g).

Workup

  1. stirringAfter stirring for 25 minutes at -75° C.
  2. customthe reaction was quenched by the addition of 0.5 M pH 5.5 monobasic potassium phosphate buffer (60 ml)
  3. additiondiluted with ethyl acetate-water
  4. additiondiluted with ethyl acetate-water
  5. extractionextracted with ethyl acetate (three times)
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-43c1d1a631c64667b8481d65a8145a42
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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