Barium hydroxide, monohydrate → (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(5-methoxy-2-(pent-4-enyl)benzylamino)butan-2-ol

HRID 501711

반응식

HRID 501711 반응식
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:16][C@H:17]([NH:36]C(=O)OCC2C=CC=CC=2)[C@H:18]([OH:35])[CH2:19][NH:20][CH2:21][C:22]2[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=2[CH2:30][CH2:31][CH2:32][CH:33]=[CH2:34])[CH:12]=[C:13]([F:15])[CH:14]=1.O.[OH-].[Ba+2].[OH-]>COCCOC.O>[NH2:36][C@@H:17]([CH2:16][C:11]1[CH:12]=[C:13]([F:15])[CH:14]=[C:9]([F:8])[CH:10]=1)[C@H:18]([OH:35])[CH2:19][NH:20][CH2:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:23]=1[CH2:30][CH2:31][CH2:32][CH:33]=[CH2:34]

참가 물질

5

반응물 2

HCID 17749100Barium hydroxide, monohydrateHCID 86622340Benzyl (2s,3r)-1-(3,5-difluorophenyl)-3-hydroxy-4-(5-methoxy-2-(pent-4-enyl)benzylamino)butan-2-ylcarbamate trifluoroacetate salt

생성물 1

HCID 59423838(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(5-methoxy-2-(pent-4-enyl)benzylamino)butan-2-ol수율 80.9%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
110 °C

실험 절차

Step AH (6): To a solution of benzyl (2S,3R)-1-(3,5-difluorophenyl)-3-hydroxy-4-(5-methoxy-2-(pent-4-enyl)benzylamino)butan-2-ylcarbamate trifluoroacetate salt (91.3 mg, 0.140 mmol) in DME (9.0 mL) and water (6.0 mL) was added barium hydroxide monohydrate (831.2 mg, 4.389 mmol). The reaction mixture was stirred at 110° C. in a high-pressure vial for 18 h. The reaction was filtered through a pad of celite and the filtrate was concentrated in vacuum. The residue was purified by silica gel chromatography to give (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-(5-methoxy-2-(pent-4-enyl)benzylamino)butan-2-ol double trifluoroacetate salt (45.8 mg, 52%) as colorless oil. LC-MS (M+H)+=405.42. 1H NMR (CD3OD, 500 MHz) δ 7.30-6.75 (m, 6H) 5.86 (m, 1H) 5.02 (m, 2H) 4.33 (m, 1H) 3.81 (s, 3H) 3.72 (m, 2H) 3.37 (m, 1H) 3.12-2.92 (m, 2H) 2.75-2.60 (m, 2H) 2.14 (m, 2H) 1.65 (m, 2H) 1.53 (m, 2H).

후처리

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated in vacuum
  3. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-f15da352e5b64ec7a47b3ae67c356c99
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772221B2

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