Water → methyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate

HRID 652326Notes

Reaction equation

HRID 652326 reaction equation
B(Br)(Br)Br.[C:5]([C:8]1[CH:31]=[CH:30][C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([NH:23][C:24](=[O:29])[C:25]([O:27][CH3:28])=[O:26])[CH:20]=[CH:21][CH:22]=2)=[C:10]([CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:9]=1[O:38]C)(=[O:7])[CH3:6].O>C(Cl)Cl>[C:5]([C:8]1[CH:31]=[CH:30][C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]([NH:23][C:24](=[O:29])[C:25]([O:27][CH3:28])=[O:26])[CH:20]=[CH:21][CH:22]=2)=[C:10]([CH2:32][CH2:33][C:34]([F:36])([F:35])[F:37])[C:9]=1[OH:38])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 19818626methyl N-{{3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate

Product 1

HCID 19818617methyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 g of boron tribromide are added dropwise to a solution, cooled to -78° C., of 2.2 g of methyl N-{{3-{3-[4-acetyl-3-methoxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate in 20 ml of methylene chloride in the course of 5 minutes. The mixture is then stirred at room temperature for 6 hours. 5 ml of water are added, with cooling, and the organic phase is separated off and evaporated under reduced pressure. Recrystallisation from methylene chloride/ether gives methyl N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-phenyl}}-oxamate.

Workup

  1. temperaturewith cooling
  2. customthe organic phase is separated off
  3. customevaporated under reduced pressure
  4. customRecrystallisation from methylene chloride/ether

Sources & evidence

ORD record
ord-e98a402e487945be976263c3d203117b
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

Loading…