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Diisopropylethylamine → 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-4-yl)sulfanyl)propanoate

HRID 2277260
ノート
印刷プレビュー

反応式

HRID 2277260 の反応式
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.[C:15]([NH:18][C@@H:19]([CH3:43])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([S:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH:35]([CH2:40][CH3:41])[CH2:36][CH2:37][CH2:38][CH3:39])=[O:32])[C:25]([NH2:42])=[CH:24][N:23]=1)(=[O:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>O.CN(C=O)C>[C:15]([NH:18][C@@H:19]([CH3:43])[CH2:20][O:21][C:22]1[CH:27]=[C:26]([S:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH:35]([CH2:40][CH3:41])[CH2:36][CH2:37][CH2:38][CH3:39])=[O:32])[C:25]([NH:42][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)=[CH:14][CH:13]=2)=[CH:24][N:23]=1)(=[O:17])[CH3:16]
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

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 226453014-(Cyclopropylmethoxy)benzoic acidHCID 867313332-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-aminopyridin-4-yl)sulfanyl)propanoate

生成物 1

HCID 86731335
2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-((4-(cyclopropylmethoxy)benzoyl)amino)pyridin-4-yl)sulfanyl)propanoate
収率 52.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A mixture of 4-(cyclopropylmethoxy)benzoic acid (452 mg), 2-ethylhexyl 3-((2-(((2S)-2-acetamidopropyl)oxy)-5-aminopyridin-4-yl)sulfanyl)propanoate (1.00 g), HATU (0.893 g), N,N-diisopropylethylamine (0.821 mL) and DMF (10 mL) was stirred at 70° C. for 5 days. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.740 g).

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-c97186785b6d4da38de27f7b4fb28cd5
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09133129B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート