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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
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HRID 1033443 반응식
[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]
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참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5843a026901c481687935262fd15f357
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05310737

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