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Potassium Bromide → (R)-3-((S)-2-(4,4-Dimethyl-3-(4-(3-phenylureido)benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-methylpropanal

HRID 1059830
Notes
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Reaction equation

HRID 1059830 reaction equation
[CH3:1][C:2]1([CH3:39])[C:6](=[O:7])[N:5]([C@@H:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:9]([NH:11][C@H:12]([CH3:16])[CH2:13][CH2:14][OH:15])=[O:10])[C:4](=[O:21])[N:3]1[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])=[CH:25][CH:24]=1.[Br-].[K+].CC(NC1CC(C)(C)N([O])C(C)(C)C1)=O.Cl[O-].[Na+].C(=O)([O-])O.[Na+]>C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[CH3:39][C:2]1([CH3:1])[C:6](=[O:7])[N:5]([C@@H:8]([CH2:17][CH:18]([CH3:20])[CH3:19])[C:9]([NH:11][C@H:12]([CH3:16])[CH2:13][CH:14]=[O:15])=[O:10])[C:4](=[O:21])[N:3]1[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:31])=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 5

HCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 5189884-Acetamido-TEMPOHCID 23665760Sodium HypochloriteHCID 69940695(R)-3-((S)-2-(4,4-Dimethyl-3-(4-(3-phenylureido)-benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-methylpropanol

Product 1

HCID 59977126
(R)-3-((S)-2-(4,4-Dimethyl-3-(4-(3-phenylureido)benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-methylpropanal

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

56.5 mg of (R)-3-((S)-2-(4,4-Dimethyl-3-(4-(3-phenylureido)-benzyl)-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetylamino)-3-methylpropanol were dissolved in a mixture of 3 ml of ethyl acetate, 1 ml of toluene and 1 ml of water with 10.8 mg of potassium bromide. After addition of a catalytic amount of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxyl (=4-acetamido-TEMPO), a mixture of 0.5 ml of sodium hypochlorite solution (13% strength), 0.5 ml of saturated sodium hydrogencarbonate solution and 1 ml of water was added dropwise at 0° C. The mixture was stirred at 0° C. for 25 minutes. After reaction was complete, the mixture was treated with ethyl acetate, and the organic phase was washed with sodium thiosulfate solution and dried over sodium sulfate. After filtration, the solvent was removed on a rotary evaporator and the residue was purified by reversed phase HPLC (water/acetonitrile). Yield: 15 mg.

Workup

  1. additionwas added dropwise at 0° C
  2. customAfter reaction
  3. washthe organic phase was washed with sodium thiosulfate solution
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was removed on a rotary evaporator
  7. customthe residue was purified by reversed phase HPLC (water/acetonitrile)

Sources & evidence

ORD record
ord-b8dc9457b1d24b3e9d09b55f25041364
Source dataset
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06521654B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes