Benzoic Acid → HCID 57068111, compound

HRID 1075224Notes

Reaction equation

HRID 1075224 reaction equation
[OH:1][C@H:2]([C@@H:4]1[C@@H:7]([S:8][CH3:9])[N:6]([C:10]([C:14]([O:16][CH3:17])=[O:15])=[C:11]([CH3:13])[CH3:12])[C:5]1=[O:18])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38](O)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:38]([O:1][C@@H:2]([C@@H:4]1[C@@H:7]([S:8][CH3:9])[N:6]([C:10]([C:14]([O:16][CH3:17])=[O:15])=[C:11]([CH3:12])[CH3:13])[C:5]1=[O:18])[CH3:3])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54037766HCID 54037766, compound

Product 1

HCID 57068111HCID 57068111, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 2 ml of tetrahydrofuran were dissolved (3S, 4R)-3-[(S)-1-hydroxyethyl]-1-(1-methoxycarbonyl-2-methylprop-1-enyl)-4-methylthioazetidin-2-one (105 mg, 0.38 mmole), triphenylphosphine (201 mg, 2 equivalents) and benzoic acid (94 mg, 2 equivalents). To the resulting solution was added little by little a solution of diethyl azodicarboxylate (134 mg, 2 equivalents) in tetrahydrofuran (1 ml) at 20° C. over 10 minutes and then the mixture was stirred at the same temperature for 1.5 hours. The solvent was then distilled off and the residue was dissolved in 3 ml of a 6:1 by volume mixture of benzene and ethyl acetate and left to stand in a refrigerator. The resulting precipitate was filtered off and the filtrate was subjected to thin layer chromatography developed with a 5:1 by volume mixture of benzene and ethyl acetate to afford 119 mg (yield 82%) of the desired product as an oil, containing a small amount of the 1'S-isomer.

Workup

  1. distillationThe solvent was then distilled off
  2. dissolutionthe residue was dissolved in 3 ml of a 6:1 by volume mixture of benzene and ethyl acetate
  3. waitleft
  4. filtrationThe resulting precipitate was filtered off
  5. additiondeveloped with a 5:1 by volume mixture of benzene and ethyl acetate

Sources & evidence

ORD record
ord-55d6637b809d429aa2984768b29c1c89
Source dataset
uspto-grants-1983_07
Patent number
US04395418

Reaction notes

Loading…