1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178502733、化合物

HRID 1036534ノート

反応式

HRID 1036534 の反応式
[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.CCN=C=NCCCN(C)C.CCN(C(C)C)C(C)C.Cl.[CH3:32][NH:33][O:34][CH3:35]>C(Cl)Cl.O>[OH:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([N:33]([O:34][CH3:35])[CH3:32])=[O:10])[CH2:6][CH2:7]1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 178525779HCID 178525779、化合物

生成物 1

HCID 178502733HCID 178502733、化合物収率 46.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Cis-4-hydroxycyclohexanecarboxylic acid (6 g, 0.042 mol) and EDCI (9.6 g, 0.05 mol, 1.2 eq.) were dissolved in DCM (100 mL) at 0° C. and stirred for 10 min. DIPEA (16 mL, 0.126 mol, 3.0 eq.) and N,O-dimethylhydroxylamine hydrochloride (4.44 g, 0.046 mol, 1.1 eq.) were added to the mixture at 0° C. The mixture was warmed to room temperature and stirred for 15 h., water was added and the mixture was extracted with DCM. The organic layer was concentrated and purified by silica gel column chromatography using DCM/CH3OH (10/1) to give product as a colorless oil (3.685 g, 40%). 1H NMR (400 MHz, CDCl3) δ: 4.01 (s, 1H), 3.70 (s, 3H), 3.18 (s, 3H), 2.72-2.69 (m, 1H), 1.98-1.85 (m, 4H), 1.62-1.55 (m, 4H).

後処理

  1. stirringstirred for 15 h.
  2. extractionthe mixture was extracted with DCM
  3. concentrationThe organic layer was concentrated
  4. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-2b1a728a7aa64d6aa9ea183c5a078ecd
出典データセット
uspto-grants-2013_10
特許番号
US08546359B2

反応ノート

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