4-Methylmorpholine → HCID 178501437、化合物

HRID 526813ノート

反応式

HRID 526813 の反応式
[C:1]([O:5][C:6]([N:8]=[C:9]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16](O)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C@@H:40]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:41]([O:43][CH3:44])=[O:42].CN1CCOCC1.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C(Cl)Cl.O>[C:31]([O:30][C:28]([NH:27][C:9]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16](=[O:17])[NH:35][CH2:36][CH2:37][CH2:38][CH2:39][C@@H:40]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[C:41]([O:43][CH3:44])=[O:42])=[N:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:29])([CH3:32])([CH3:33])[CH3:34]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 29926888(R)-Methyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoateHCID 178454264HCID 178454264、化合物

生成物 1

HCID 178501437HCID 178501437、化合物収率 73.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of acid 8 (1.95 g, 4.00 mmol) and amine 14 (1.04 g, 4.00 mmol) in CH2Cl2 (60 mL) was charged with NMM (2.64 mL, 24.0 mmol) and EEDQ (1.97 g, 8.00 mmol). The resulting mixture was stirred at room temperature for 16 h. Water (20 mL) was added to the reaction mixture and extracted with CH2Cl2 (3×50 mL). The combined organic extract was washed with brine and dried over Na2SO4. The solvent was removed and the residue was purified by column chromatography (silica gel, 20% to 40% EtOAc in hexanes) to afford amide 15 (2.15 g, 73% over two steps) as a white solid: 1H NMR (400 MHz, CD3OD) δ 4.10-4.02 (m, 1H), 4.01-3.92 (m, 1H), 3.70 (s, 3H), 3.35 (t, J=6.8 Hz, 2H), 3.24-3.10 (m, 2H), 1.83-1.67 (m, 2H), 1.66-1.55 (m, 4H), 1.52 (s, 9H), 1.46 (s, 9H), 1.45-1.35 (m, 6H), 1.438 (s, 9H), 1.431 (s, 9H).

後処理

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe residue was purified by column chromatography (silica gel, 20% to 40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-8158aeebfe334fb8877065ad6739d124
出典データセット
uspto-grants-2016_05
特許番号
US09346753B2

反応ノート

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