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Diisopropylethylamine → 3-[2(R)-Triethylsiloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide

HRID 1033443
ノート
印刷プレビュー

反応式

HRID 1033443 の反応式
[OH:1][C@H:2]([CH3:24])[CH2:3][NH:4][C:5]([CH3:23])([CH3:22])[CH2:6][C:7]([NH:9][C@@H:10]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[NH:12][C:11]1=[O:21])=[O:8].C(N(CC)C(C)C)(C)C.FC(F)(F)S(O[Si:40]([CH2:45][CH3:46])([CH2:43][CH3:44])[CH2:41][CH3:42])(=O)=O>C(Cl)Cl>[CH2:41]([Si:40]([CH2:45][CH3:46])([CH2:43][CH3:44])[O:1][C@H:2]([CH3:24])[CH2:3][NH:4][C:5]([CH3:23])([CH3:22])[CH2:6][C:7]([NH:9][C@@H:10]1[CH2:16][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=2[NH:12][C:11]1=[O:21])=[O:8])[CH3:42]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 186514293-[2(R)-Hydroxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide

生成物 1

HCID 186514313-[2(R)-Triethylsiloxypropyl]amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide収率 72.3%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To a stirred solution of 660 mg (1.48 mmol) of the intermediate obtained in Step B in 3 mL of methylene chloride at room temperature was added 1.1 mL of N,N-diisopropylethylamine (0.81 g, 4.2 eq.) followed by 0.71 mL of triethylsilyl trifluoromethanesulfonate (0.83 g, 2.1 eq.). The resulting mixture was stirred at room temperature for 2 hours then partitioned between ethyl acetate and saturated aqueous sodium chloride (buffered to pH 9 with 2 drops of ammonium hydroxide). The organic layer was separated, washed with buffered brine, dried over magnesium sulfate, filtered and solvents evaporated under vacuum. The residue was purified by preparative high pressure liquid chromatography on silica, eluting with ethyl acetate/0.1% ammonium hydroxide in methanol (85:15), to afford 480 mg (1.07 mmol, 72%) of product. 1H NMR (200 MHz,CD3OD): 0.63 (q,8 Hz,6H), 0.97 (t,8 Hz,9H), 1.14 (s,6H), 1.18 (d,6 Hz,3H), 2.05 (m,1H), 2.28 (d,2Hz,2H), 2.35-3.00 (m,5H), 4.01 (m,1H), 4.44 (dd;8,12 Hz;1H), 7.05 (d,8 Hz,1H), 7.10-7.35 (m,3H). FAB-MS: calculated for C24H41N3O3Si 447; found 448 (M+H, 100%).

後処理

  1. customthen partitioned between ethyl acetate and saturated aqueous sodium chloride (buffered to pH 9 with 2 drops of ammonium hydroxide)
  2. customThe organic layer was separated
  3. washwashed with buffered brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvents evaporated under vacuum
  7. customThe residue was purified by preparative high pressure liquid chromatography on silica
  8. washeluting with ethyl acetate/0.1% ammonium hydroxide in methanol (85:15)

出典と根拠

ORDレコード
ord-5843a026901c481687935262fd15f357
出典データセット
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05310737

反応ノート

読み込み中…

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