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Diisopropylethylamine → HCID 53349361、化合物

HRID 2357096
ノート
印刷プレビュー

反応式

HRID 2357096 の反応式
[C:1]([O:5][C:6]([N:8]1[C@@:12]([CH3:16])([C:13]([OH:15])=O)[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[CH2:52]([O:60][C:61]1[CH:70]=[CH:69][C:64]([C:65]([NH:67][NH2:68])=[O:66])=[CH:63][C:62]=1[C:71]([F:74])([F:73])[F:72])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59]>C(OCC)(=O)C.C(Cl)Cl.CN(C=O)C>[CH3:17][C:9]1([CH3:18])[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@:12]([CH3:16])([C:13]([NH:68][NH:67][C:65](=[O:66])[C:64]2[CH:69]=[CH:70][C:61]([O:60][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])=[C:62]([C:71]([F:72])([F:74])[F:73])[CH:63]=2)=[O:15])[CH2:11][O:10]1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531Diisopropylethylamine2 回HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2 回HCID 52987736HCID 52987736、化合物2 回HCID 533493604-(Octyloxy)-3-(trifluoromethyl)benzohydrazide2 回

生成物 1

HCID 53349361HCID 53349361、化合物
収率 92.1%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 22350042dichloromethane N,N-dimethylformamide溶媒2 回

実験手順

(R)-3-(tert-Butoxycarbonyl)-2,2,4-trimethyloxazolidine-4-carboxylic acid (D7) (210 mg, 0.81 mmol), HATU (372 mg, 0.98 mmol), diisopropylethyl amine (DIEA) (0.705 mL, 4.1 mmol), CH2Cl2-DMF and 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (D6) (270 mg, 0.81 mmol) were mixed together. The reaction was condensed, diluted with ethyl acetate, washed with water and brine, and condensed again. Another batch was made using this method with (D7) (0.1 mmol), HATU (46 mg, 0.12 mmol), DIEA (87 mL, 0.5 mmol), CH2Cl2-DMF and 4-(octyloxy)-3-(trifluoromethyl)benzohydrazide (D6) (>6 mg, 0.1 mmol). The batches were chromatographed and combined to provide the title product (428 mg). MS (ESI): 573.84 (MH+); 1H NMR (400 MHz, CDCl3) δ 9.43 (br, 2H), 8.06 (d, 1H, J=2.0 Hz), 7.94 (dd, 1H, J=8.8 Hz, J=2.0 Hz), 6.96 (d, 1H, J=8.8 Hz), 4.52 (br, 1H), 4.07 (t, 2H, J=6.4 Hz), 3.76 (br, 1H), 1.82 (m, 2H), 1.67 (s, 6H), 1.57 (s, 3H), 1.51 (s, 9H), 1.51-1.43 (m, 4H), 1.38-1.24 (m, 6H), 0.88 (t, 3H, J=7.2 Hz).

後処理

  1. customcondensed
  2. washwashed with water and brine, and condensed again
  3. customThe batches were chromatographed

出典と根拠

ORDレコード
ord-efe41c043629430c93555eec5ee48c60
出典データセット
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07759370B2

反応ノート

読み込み中…

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