1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanamide

HRID 403584ノート

反応式

HRID 403584 の反応式
[CH3:1][C:2]([CH3:25])([CH3:24])[C@@H:3]([N:5]1[CH2:10][CH2:9][C@:8]([CH2:18][CH2:19][C:20](O)=[O:21])([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[O:7][C:6]1=[O:23])[CH3:4].CC[N:28]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][C:2]([CH3:25])([CH3:24])[C@@H:3]([N:5]1[CH2:10][CH2:9][C@:8]([CH2:18][CH2:19][C:20]([NH2:28])=[O:21])([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[O:7][C:6]1=[O:23])[CH3:4]

参加物

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 584852693-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanoic acid

生成物 1

HCID 426422863-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanamide収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanoic acid (50 mg, 0.144 mmol), EDCI (55 mg, 0.28 mmol), HOBt (38 mg, 0.28 mmol), and DIEA (90 mg, 0.07 mmol) were dissolved in CH2Cl2 (10 mL) under ice bath. The mixture was stirred under an NH3 atmosphere overnight. The reaction mixture was concentrated to give the crude product, which was purified by preparative TLC to give 3-((R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propanamide (15 mg, 30%). LC-MS Method 1 tR=2.027, min, m/z=351.1; 1H NMR (CDCl3) 0.73 (s, 9H), 1.12 (d, 3H), 1.89-1.98 (m, 1H), 2.01-2.12 (m, 1H), 2.22-2.38 (m, 3H), 2.48-2.52 (m, 1H), 2.71 (m, 1H), 3.18 (m, 1H), 4.46 (m, 1H), 5.29 (s, 1H), 5.53 (s, 1H), 7.07 (m, 2H), 7.29 (m, 2H)

後処理

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by preparative TLC

出典と根拠

ORDレコード
ord-4ca6af5c05b847d8b5bdffa0233e6012
出典データセット
uspto-grants-2014_06
特許番号
US08748444B2

反応ノート

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