Acetic Acid → N-[3-(Methylsulfanyl)-2-oxoazetidin-3-yl]-2-phenoxyacetamide

HRID 246861Notes

Reaction equation

HRID 246861 reaction equation
[Si]([N:8]1[CH2:11][C:10]([S:23][CH3:24])([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]1=[O:25])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C.C(OCC)(=O)C>O1CCCC1.O>[CH3:24][S:23][C:10]1([NH:12][C:13](=[O:22])[CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][NH:8][C:9]1=[O:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 20162855HCID 20162855, compound

Product 1

HCID 20162876N-[3-(Methylsulfanyl)-2-oxoazetidin-3-yl]-2-phenoxyacetamideYield 101.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (24) (516 mg) in dry tetrahydrofuran (THF) (10 ml) was cooled to -10° C. and treated with tetrabutylammonium fluoride (476 mg) and glacial acetic acid (180 mg) in a minimum volume of dry THF. After approximately 15 mins the mixture was poured into a mixture of ethyl acetate and water. The organic phase was separated and washed successively with dilute sodium bicarbonate, dilute hydrochloric acid, and brine, then dried and evaporated. Chromatography on silica gel gave the product (25) (366 mg), a white solid. νmax 3410, 1775 and 1690 cm-1 ; δppm (CDCl3) (90 MHz) 2.24 (s, 3 H), 3.48 and 3.90 (ABq, 2H, J7.0 Hz), 4.50 (s, 2H), 6.24 (s, 1H, exch.), 6.80 to 7.45 (m, 6H, becomes m, 5H, on exch.)

Workup

  1. customThe organic phase was separated
  2. washwashed successively with dilute sodium bicarbonate, dilute hydrochloric acid, and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-b9cfee5327b744c29b98319de41900db
Source dataset
uspto-grants-1987_11
Patent number
US04704385

Reaction notes

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