4-Methylmorpholine → HCID 178501437, 화합물

HRID 526813노트

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HRID 526813 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 178501437HCID 178501437, 화합물수율 73.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-8158aeebfe334fb8877065ad6739d124
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346753B2

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