Nitrogen → HCID 11669308, compound

HRID 852345Notes

Reaction equation

HRID 852345 reaction equation
[O:1]=[O+][O-].[CH3:4][C:5]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:33])[CH:17]([NH:21][C:22](=[O:32])[CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)[CH2:18][CH2:19][CH3:20])=[N:12][N:11]=1)([CH3:9])[CH2:6][CH:7]=C.N#N>C(Cl)Cl>[CH3:4][C:5]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:33])[CH:17]([NH:21][C:22](=[O:32])[CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)[CH2:18][CH2:19][CH3:20])=[N:12][N:11]=1)([CH3:9])[CH2:6][CH:7]=[O:1]

Participants

5

Reactant 3

HCID 947NitrogenHCID 24823Ozone2×HCID 11539372HCID 11539372, compound

Product 1

HCID 11669308HCID 11669308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A stream of ozone was generated and passed through a solution of 2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoic acid [5-(1,1-dimethyl-but-3-enyl)-[1,3,4]thiadiazol-2-yl]-amide (631 mg, 1.445 mmol) in 40 ml of methylene chloride until the mixture turned to blue solution or until the disappearance of starting material at −78° C. The mixture was stirred at −78° C. for 10 min, then the excess ozone was replaced with N2 at −78° C. The mixture was quenched with excess of dimethylsulfide and stirred at r.t. overnight. The mixture was concentrated to dryness, purified by Shimadzu HPLC to give the title compound as a yellow solid, RT=2.3 min, M+1=439.5.

Workup

  1. customturned to blue solution or until the disappearance of starting material at −78° C
  2. customThe mixture was quenched with excess of dimethylsulfide
  3. stirringstirred at r.t. overnight
  4. concentrationThe mixture was concentrated to dryness
  5. custompurified by Shimadzu HPLC

Sources & evidence

ORD record
ord-173b7b52bfd149a9abbaec7bfedac0aa
Source dataset
uspto-grants-2007_08
Patent number
US07253195B2

Reaction notes

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