p-Toluenesulfonic acid monohydrate → Ammonium Acetate

HRID 78430

反応式

HRID 78430 の反応式
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[C:6]([N:8]=[C:9]1[N:13]([CH2:14][CH2:15][O:16][CH3:17])[C:12]2(OCC)[CH2:18][O:19][CH2:20][CH:11]2[S:10]1)=[O:7])[CH3:2].O.C1(C)C=CC(S(O)(=O)=[O:36])=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:20]([O-:36])(=[O:19])[CH3:11].[NH4+:8].[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[C:6]([N:8]=[C:9]1[N:13]([CH2:14][CH2:15][O:16][CH3:17])[C:12]2[CH2:18][O:19][CH2:20][C:11]=2[S:10]1)=[O:7])[CH3:2]

参加物

6

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 686235912-Ethoxy-N-[3a-ethoxy-3-(2-methoxy-ethyl)-tetrahydro-furo[3,4-d]thiazol-2-ylidene]-benzamide

生成物 2

HCID 517165Ammonium AcetateHCID 248978442-Ethoxy-N-[3-(2-methoxyethyl)-4,6-dihydro-3H-furo[3,4-d]thiazol-2-ylidene]-benzamide

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the product from Example 125D (15 mg, 0.04 mmol) in toluene (10 mL) was added p-toluenesulfonic acid monohydrate (2 mg). The mixture was refluxed for 3 hours and then cooled to room temperature, diluted with ethyl acetate, washed with 1M NaHCO3, dried (Na2SO4), filtered and concentrated. Purification by preparative HPLC on a waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile: ammonium acetate (10 mM) over 15 min at a flow rate of 70 mL/min afforded the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (t, J=7.0 Hz, 3H), 3.24 (s, 3H), 3.65 (t, J=4.9 Hz, 2H), 4.07 (q, J=6.8 Hz, 2H), 4.25 (t, J=5.1 Hz, 2H), 4.96 (s, 4H), 6.92-7.01 (m, 1H), 7.07 (d, J=8.1 Hz, 1H), 7.36-7.44 (m, 1H), 7.74 (dd, J=7.5, 1.7 Hz, 1H); MS (ESI+) m/z 349 (M+H)+.

後処理

  1. temperatureThe mixture was refluxed for 3 hours
  2. washwashed with 1M NaHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by preparative HPLC on a waters Symmetry C8 column (40 mm×100 mm, 7 μm particle size)

出典と根拠

ORDレコード
ord-90fc50378e2f470ca890d6833d05d5d6
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

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