Diethylamine → HCID 87352571、化合物

HRID 1012858

反応式

HRID 1012858 の反応式
[CH3:1][O:2][C:3](=[O:55])[CH2:4][NH:5][C:6](=[O:54])[C@H:7]([NH:11][C:12](=[O:53])[C@H:13](NC(OCC1C2C=CC=CC=2C2C1=CC=CC=2)=O)[CH2:14][S:15][C:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:8]([CH3:10])[CH3:9].[NH:56](CC)CC.[C:61]([NH:78][C@@H:79]([C:87]([OH:89])=O)[CH2:80][C:81]1[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=1)([O:63][CH2:64][CH:65]1[C:77]2[C:72](=[CH:73][CH:74]=[CH:75][CH:76]=2)[C:71]2[C:66]1=[CH:67][CH:68]=[CH:69][CH:70]=2)=[O:62].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CC#N.C(Cl)Cl.CCCCCCC.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:55])[CH2:4][NH:5][C:6](=[O:54])[C@H:7]([NH:11][C:12](=[O:53])[C@H:13]([NH:56][C:87](=[O:89])[C@H:79]([NH:78][C:61]([O:63][CH2:64][CH:65]1[C:70]2[CH:69]=[CH:68][CH:67]=[CH:66][C:71]=2[C:72]2[C:77]1=[CH:76][CH:75]=[CH:74][CH:73]=2)=[O:62])[CH2:80][C:81]1[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=1)[CH2:14][S:15][C:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:8]([CH3:10])[CH3:9]

参加物

10

反応物 6

HCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 978332(2R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57696983HCID 57696983、化合物

生成物 1

HCID 87352571HCID 87352571、化合物収率 80%

試薬・触媒・溶媒 3

HCID 6344Dichloromethane溶媒2 回HCID 8900Heptane溶媒HCID 21877088Acetonitrile methylene chloride溶媒

実験手順

To a stirred solution of 3A (836 mg, 1.11 mmol) in CH3CN/CH2Cl2 (1:1, 60 mL) at RT was added Et2NH (3 mL). After stirring for 3 h at RT the reaction mixture was diluted with heptane (60 mL) and concentrated to give the crude amine as a colourless oil. To a stirred solution of Fmoc-D-phenylalanine (650 mg, 1.7 mmol) in CH2Cl2 (30 mL) was added EDAC.HCl (326 mg, 1.7 mmol), HOBt (230 mg, 1.7 mmol) and DIEA (627 μl, 3.6 mmol). After stirring at RT for 10 minutes a solution of the crude amine in CH2Cl2 (20 mL) was then added and the reaction mixture stirred for 12 h. Whereupon the reaction was washed with water (15 mL), 10% HCl (15 mL), 5% NaHCO3 (15 mL) and sat NaCl (15 mL) solutions, dried (Na2SO4), filtered, and the solvent removed to give an off white solid which was recrystallised from CH3CN to give 4B as a white solid (800 mg, 0.89 mmol, 80%): IR νmax 3264, 3053, 1742, 1701, 1636, 1532 cm−1; 1H-NMR (400 MHz, CDCl3) δ 7.75 (d, J=7.5 Hz, 2H), 7.46 (t, J=7.5 Hz, 2H), 7.41-7.31 (m, 8H), 7.30-7.07 (m, 16H), 7.01 (br s, 1H), 6.54 (br s, 2H), 5.29 (br s, 1H), 4.48-4.32 (m, 3H), 4.25-4.13 (m, 1H), 4.10 (t, J=8.5 Hz, 1H), 3.99-3.76 (m, 3H), 3.65 (s, 3H), 3.10-2.88 (m, 2H), 2.83-2.69 (m, 1H), 2.49 (dd, J=13.0, 6.3 Hz, 1H), 2.36-2.22, (m, 1H), 0.93 (t, J=7.0 Hz, 6H); 13C NMR 100 MHz 171.2 (C), 171.0 (C), 170.2 (C), 170.0 (C), 156.2 (C), 144.3 (C), 143.9 (C), 143.7 (C), 141.4 (C), 136.0 (C), 129.5 (CH), 129.3 (CH), 129.0 (CH), 128.3 (CH), 127.9 (CH), 127.4 (CH), 127.2 (CH), 127.1 (CH), 125.2 (CH), 120.1 (CH), 67.3 (CH2), 58.6 (CH), 56.2 (CH), 52.8 (CH), 52.3 (CH3), 47.2 (CH), 41.0 (CH2), 38.3 (CH2), 33.5 (CH2), 30.2 (CH), 19.4 (CH3), 17.7 (CH3); LRMS (ES+) m/z 1828 (30%, [2M+Na]+), 925 (100%, [M+Na]+).

後処理

  1. concentrationconcentrated
  2. customto give the crude amine as a colourless oil
  3. additionwas then added
  4. stirringthe reaction mixture stirred for 12 h
  5. washWhereupon the reaction was washed with water (15 mL), 10% HCl (15 mL), 5% NaHCO3 (15 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent removed
  9. customto give an off white solid which
  10. customwas recrystallised from CH3CN

出典と根拠

ORDレコード
ord-f283058fda2143228931e03329e0ebf8
出典データセット
uspto-grants-2011_07
特許番号
US07977304B2

関連ノート

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