Diisopropylethylamine → tert-butyl ((2S,3R)-1-((2S,4R)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate

HRID 1852123

反応式

HRID 1852123 の反応式
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][C@@H:33]([C@H:45]([CH3:53])[CH2:46][CH:47]([CH3:52])[CH2:48][CH2:49][CH:50]=[CH2:51])[C:34]([N:36]1[CH2:40][C@H:39]([OH:41])[CH2:38][C@H:37]1[C:42]([OH:44])=[O:43])=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:65][C@:66]1([C:71]([NH:73][S:74]([CH:77]2[CH2:79][CH2:78]2)(=[O:76])=[O:75])=[O:72])[CH2:68][C@H:67]1[CH:69]=[CH2:70].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:77]1([S:74]([NH:73][C:71]([C@@:66]23[CH2:68][C@H:67]2[CH:51]=[CH:50][CH2:49][CH2:48][CH:47]([CH3:52])[CH2:46][C@@H:45]([CH3:53])[C@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:27])([CH3:26])[CH3:28])[C:34](=[O:35])[N:36]2[CH2:40][C@H:39]([OH:41])[CH2:38][C@H:37]2[C:42](=[O:44])[NH:65]3)=[O:72])(=[O:76])=[O:75])[CH2:79][CH2:78]1.[CH:77]1([S:74]([NH:73][C:71]([C@@:66]2([NH:65][C:42]([C@@H:37]3[CH2:38][C@@H:39]([OH:41])[CH2:40][N:36]3[C:34](=[O:35])[C@@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:26])([CH3:28])[CH3:27])[C@H:45]([CH3:53])[CH2:46][CH:47]([CH3:52])[CH2:48][CH2:49][CH:50]=[CH2:51])=[O:43])[CH2:68][C@H:67]2[CH:69]=[CH2:70])=[O:72])(=[O:76])=[O:75])[CH2:79][CH2:78]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 721632271028252-16-5HCID 86683196HCID 86683196、化合物

生成物 2

HCID 89550183tert-Butyl ((2R,6S,7R,13 aS,14aR,16aS,Z)-14a-((cyclopropylsulfonyl)carbamoyl)-2-hydroxy-7,9-dimethyl-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecin-6-yl)carbamateHCID 89550268tert-butyl ((2S,3R)-1-((2S,4R)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate収率 187.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

HATU (11.54 g, 30.4 mmol) was added to a solution of (2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid (10.44 g, 25.3 mmol), (1R,2S)-1-amino-N-(cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide, p-toluenesulfonate salt (11.17 g, 27.8 mmol), and Hunig's Base (17.67 ml, 101 mmol) in DCM (200 ml) and was stirred at RT for overnight. The reaction was washed with 1N HCl (3×) and then brine and evaporated on rotovap, and purified to get the final product tert-butyl ((2S,3R)-1-((2S,4R)-2-(((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate (14.8 g, 23.69 mmol, 94% yield) as a light orange foam.

後処理

  1. washThe reaction was washed with 1N HCl (3×)
  2. custombrine and evaporated on rotovap
  3. custompurified

出典と根拠

ORDレコード
ord-f06fb1df6e6c42e7b017f2125447d7bc
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

関連ノート

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