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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
ノート
印刷プレビュー

反応式

HRID 1059830 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 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

生成物 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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b8dc9457b1d24b3e9d09b55f25041364
出典データセット
uspto-grants-2003_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06521654B2

反応ノート

読み込み中…

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