Triethylamine → Carbamate

HRID 1852121

反応式

HRID 1852121 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)=[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]1C=C.C(N(CC)CC)C>C(Cl)Cl>[F:71][CH2:70][C:67]1([S:64]([NH:63][C:61]([C@@:56]23[CH2:58][C@H:57]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]([CH3:26])([CH3:28])[CH3:27])[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:55]3)=[O:62])(=[O:66])=[O:65])[CH2:68][CH2:69]1.[C:30](=[O:29])([O-:31])[NH2:32]

参加物

7

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 2

HCID 276Carbamate収率 1,959.7%HCID 71005415HCID 71005415、化合物

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 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), and triethylamine (14.19 mL, 102 mmol) in DCM (220 mL) and was stirred at RT for overnight. The reaction was washed with 1N HCl (3×) and then 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. custombrine 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-3622bbc10ce544599b9a5b1645adc8d7
出典データセット
uspto-grants-2015_02
特許番号
US08957203B2

関連ノート

読み込み中…