Triethylamine → HCID 86683251、化合物

HRID 1481655

反応式

HRID 1481655 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](O)=[O:43])=[O:35])=[O:31])([CH3:28])([CH3:27])[CH3:26].Cl.[NH2:55][C@:56]1([C:61]([NH:63][S:64]([C:67]2([CH2:70][F:71])[CH2:69][CH2:68]2)(=[O:66])=[O:65])=[O:62])[CH2:58][C@H:57]1[CH:59]=[CH2:60].C(N(CC)CC)C>C(Cl)Cl>[C:25]([O:29][C:30](=[O:31])[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](=[O:43])[NH:55][C@:56]1([C:61](=[O:62])[NH:63][S:64]([C:67]2([CH2:70][F:71])[CH2:69][CH2:68]2)(=[O:66])=[O:65])[CH2:58][C@H:57]1[CH:59]=[CH2:60])=[O:35])([CH3:28])([CH3:27])[CH3:26]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86683196(2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acidHCID 86683199(1R,2S)-1-amino-N-(1-(fluoromethyl)cyclopropylsulfonyl)-2-vinylcyclopropanecarboxamide hydrochloride

生成物 1

HCID 86683251HCID 86683251、化合物収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

HATU (11.61 g, 30.5 mmol) was added to a DCM (220 mL) solution of (2S,4R)-1-((2S,3R)-2-((tert-butoxycarbonyl)amino)-3,5-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid (10.50 g, 25.5 mmol), (1R,2S)-1-amino-N-((1-(fluoromethyl)cyclopropyl)sulfonyl)-2-vinylcyclopropanecarboxamide HCl (8.37 g, 28 mmol), triethylamine (14.19 mL, 102 mmol). The reaction mixture was stirred at RT for overnight. The reaction was washed with 1N HCl (3×) and then with brine and evaporated on rotovap. The crude material was purified by silica gel chromatography using 20-40% Acetone in hexanes. The product fractions were collected and the solvent removed under vacuum to give the desired product tert-butyl((2S,3R)-1-((2S,4R)-2-(((1R,2S)-1-(((1-(fluoromethyl)cyclopropyl)sulfonyl)carbamoyl)-2-vinylcyclopropyl)carbamoyl)-4-hydroxypyrrolidin-1-yl)-3,5-dimethyl-1-oxonon-8-en-2-yl)carbamate (15 g, 90% yield). MS: MS m/z 657.3 (M++1).

後処理

  1. washThe reaction was washed with 1N HCl (3×)
  2. customwith brine and evaporated on rotovap
  3. customThe crude material was purified by silica gel chromatography
  4. customThe product fractions were collected
  5. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-4aafaad06663455b8f1e6778b340bc7b
出典データセット
uspto-grants-2016_08
特許番号
US09409943B2

関連ノート

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