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Benzoyl Peroxide → methyl (1S)-1-({[(1S,2S,4S)-1-benzyl-2-[1-(ethylthio)ethoxy]-4-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-5-(4-pyridin-2-ylphenyl)pentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate

HRID 1174420
ノート
印刷プレビュー

反応式

HRID 1174420 の反応式
[CH3:1][O:2][C:3](=[O:51])[NH:4][C@@H:5]([C:47]([CH3:50])([CH3:49])[CH3:48])[C:6](=[O:46])[NH:7][C@@H:8]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@@H:9]([OH:38])[CH2:10][C@H:11]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][CH:27]=1)[NH:12][C:13](=[O:24])[C@H:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[NH:15][C:16](=[O:19])[O:17][CH3:18].[CH2:52]([S:54][CH2:55][CH3:56])[CH3:53].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH2:39]([C@H:8]([NH:7][C:6]([C@@H:5]([NH:4][C:3](=[O:51])[O:2][CH3:1])[C:47]([CH3:50])([CH3:49])[CH3:48])=[O:46])[C@@H:9]([O:38][CH:52]([S:54][CH2:55][CH3:56])[CH3:53])[CH2:10][C@@H:11]([NH:12][C:13](=[O:24])[C@H:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[NH:15][C:16]([O:17][CH3:18])=[O:19])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][CH:27]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 7187Benzoyl PeroxideHCID 9609Ethyl sulfideHCID 11181604methyl [(1S,4S,5S,7S,10S)-4-benzyl-1,10-di-tert-butyl-5-hydroxy-2,9,12-trioxo-7-(4-pyridin-2-ylbenzyl)-13-oxa-3,8,11-triazatetradec-1-yl]carbamate

生成物 1

HCID 86726259methyl (1S)-1-({[(1S,2S,4S)-1-benzyl-2-[1-(ethylthio)ethoxy]-4-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-5-(4-pyridin-2-ylphenyl)pentyl]amino}carbonyl)-2,2-dimethylpropylcarbamate
収率 104.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a slurry of the compound of Example 2D (2.00 g, 2.84 mmol) and ethyl sulfide (8.0 mL, 74.06 mmol) in acetonitrile (28.0 mL) at room temperature was added benzoyl peroxide (4.95 g, 20.45 mmol) in three portions over 2 hours. The reaction was diluted with ethyl acetate and washed with 10% Na2CO3 and brine. The organic was dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel eluting with a gradient starting with dichloromethane and ending with ethyl acetate to give the title compound (2.35 g, 84% yield).

後処理

  1. washwashed with 10% Na2CO3 and brine
  2. dry with materialThe organic was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was chromatographed on silica gel eluting with a gradient

出典と根拠

ORDレコード
ord-a89593cfd5d946db93f0e886dab4a5d6
出典データセット
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07834043B2

反応ノート

読み込み中…

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