Potassium Bromide → HCID 67074495, compound

HRID 2095512Notes

Reaction equation

HRID 2095512 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][OH:23])[CH2:14][C@H:13]2[CH3:24])=[O:11])[CH:5]=[CH:6][CH:7]=1.CC1(C)N([O])C(C)(C)CCC1.[Br-].[K+].Cl[O-].[Na+].C([O-])(O)=[O:42].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][C:22]([OH:42])=[O:23])[CH2:14][C@H:13]2[CH3:24])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 2724126TempoHCID 23665760Sodium HypochloriteHCID 67074020HCID 67074020, compound

Product 1

HCID 67074495HCID 67074495, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolCatalyst

Procedure

To 0.52 g (1 mmol) of (R)-1-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(3-hydroxy-propyl)-2-methyl-[1,4]diazepan-5-one, 0.002 g (0.01 mmol) TEMPO in 5 ml of ice cold CH2Cl2 was added 0.018 g (0.2 mmol) of potassium bromide in a solution of 4.6 ml (6 mmol) of 13% sodium hypochlorite saturated with NaHCO3. The mixture was rapidly stirred for 5 minutes after which time a few drops of MeOH were added and the phases separated. The aqueous was acidified with 1N HCl and repeatedly extracted with CH2Cl2, dried (Na2SO4) and concentrated. This afforded the titled compound in 92% yield as a colorless foam. MS: 365.2 (MH+, Cl).

Workup

  1. additionwere added
  2. customthe phases separated
  3. extractionrepeatedly extracted with CH2Cl2
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c12e9f57175e4cb3bd2b4b5d3aa5d6d0
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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