Methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate → HCID 57009344, compound

HRID 1090360Notes

Reaction equation

HRID 1090360 reaction equation
[Cl:1][C:2]1[C:7]([SH:8])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C@@H:20]2[O:26][C@H:21]2[C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C>[Cl:1][C:2]1[C:7]([S:8][C@@H:20]([C:17]2[CH:16]=[CH:15][C:14]([O:13][CH3:12])=[CH:19][CH:18]=2)[C@@H:21]([OH:26])[C:22]([O:24][CH3:25])=[O:23])=[C:6]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 158607Methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylateHCID 111831062-Chloro-6-nitro-benzenethiol

Product 1

HCID 57009344HCID 57009344, compound

Reagents, catalysts & solvents 2

HCID 2724192Zinc acetate (USP)CatalystHCID 1140TolueneSolvent2×

Procedure

In a 25 ml flask equipped with thermometer and nitrogen admission, there are introduced 22 mg of zinc acetate dihydrate, 948 mg of 6-chloro-2-nitrothiophenol and 5 ml of toluene. To the suspension are added dropwise, within 5 mn, a solution of 1.093 g of methyl (-) (2R,3S) 3-(4-methoxyphenyl)-2,3-epoxy-propionate in 7.5 ml of toluene at 25° C. The temperature rises to 27°-28° C., whilst stirring is maintained for 1.5 hour. The mixture is evaporated in vacuo, and a yellow oil is obtained, which is used as it is in the subsequent example.

Workup

  1. customIn a 25 ml flask equipped with thermometer and nitrogen admission, there
  2. additionTo the suspension are added dropwise, within 5 mn
  3. customat 25° C
  4. customrises to 27°-28° C.
  5. temperatureis maintained for 1.5 hour
  6. customThe mixture is evaporated in vacuo
  7. customa yellow oil is obtained

Sources & evidence

ORD record
ord-24bb32e3fe444ea6b051e3826286cadc
Source dataset
uspto-grants-1992_01
Patent number
US05081277

Reaction notes

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