Sodium Bicarbonate → benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate

HRID 501681노트

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HRID 501681 반응식
Cl([O-])(=O)(=O)=O.[Li+].[CH2:7]([O:10][CH2:11][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:13])[CH:8]=[CH2:9].[F:20][C:21]1[CH:22]=[C:23]([CH2:28][C@H:29]([NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:30]2[CH2:32][O:31]2)[CH:24]=[C:25]([F:27])[CH:26]=1.C([O-])(O)=O.[Na+]>CC#N.[Cl-].[Na+].O>[CH2:7]([O:10][CH2:11][C@H:12]([NH:13][CH2:32][C@@H:30]([OH:31])[C@@H:29]([NH:33][C:34](=[O:43])[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:28][C:23]1[CH:22]=[C:21]([F:20])[CH:26]=[C:25]([F:27])[CH:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:8]=[CH2:9]

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 10131699HCID 10131699, 화합물HCID 23665649Lithium perchlorateHCID 68465142(1R)-2-Allyloxy-1-phenyl-ethanamine

생성물 1

HCID 86622319benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate수율 72.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 57417360Sodium chloride; water용매

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온도
50 °C

실험 절차

Step Q (4): Lithium perchlorate (1.59 g, 15 mmol) was added to a solution of (R)-2-(allyloxy)-1-phenylethanamine (530 mg, 2.99 mmol) from Step Q (3) and benzyl (S)-2-(3,5-difluorophenyl)-1-((S)-oxiran-2-yl)ethylcarbamate (996 mg, 2.99 mmol) in CH3CN (10 mL). The resulting mixture was stirred at 50° C. for 16 h, then poured into a solution of brine and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to give 1.1 g (72% yield) of benzyl (2S,3R)-4-((R)-2-(allyloxy)-1-phenylethylamino)-1-(3,5-difluorophenyl)-3-hydroxybutan-2-ylcarbamate. LC-MS (M+H)+=511.5; 1H NMR (300 MHz, CDCl3) δ ppm 2.36-2.53 (m, J=10.98 Hz, 1H) 2.55-3.00 (m, 3H) 3.25-3.74 (m, 3H) 3.77-4.19 (m, 3H) 4.71-4.84 (m, 1H) 5.00 (s, 2H) 5.09-5.37 (m, 2H) 5.74-6.00 (m, 1H) 6.50-6.78 (m, 3H) 7.16-7.42 (m, 10H).

후처리

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. customdried
  4. dry with materialover dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0c74db48221a4cb89be879e6678fcbd9
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

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