Pyridine → HCID 69734019, 화합물

HRID 488357노트

반응식

HRID 488357 반응식
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][N:14]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:13][CH2:12]3)[CH2:4]1.N1C=CC=CC=1.[C:35](OC(=O)C)(=[O:37])[CH3:36]>C(Cl)Cl>[C:35]([NH:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH2:15][N:14]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:13][CH2:12]3)[CH2:4]1)(=[O:37])[CH3:36]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69733820HCID 69733820, 화합물

생성물 1

HCID 69734019HCID 69734019, 화합물수율 93.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of phenylmethyl 6-[(5S)-5-(aminomethyl)-2-oxo-3-oxazolidinyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Step 4, 1.75 g, 4.59 mmol) and pyridine (1.11 mL, 13.77 mmol) in dry CH2Cl2 (23 mL) under N2 is treated with acetic anhydride (0.649 mL, 6.88 mmol), and the mixture is stirred at ambient temperature for 3.5 hrs. The mixture is then washed with H2O (2×15 mL) and brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge, eluting with a gradient of MeOH/CH2Cl2 (0.5/99.5-2/98), and those fractions with an Rf=0.25 by TLC (MeOH/CHCl3, 5/95) are pooled and concentrated to give 1.81 g (93%) of the title compound as an amorphous, white solid. 1H NMR (400 MHz, CDCl3) δ 7.35 (m, 7H), 7.11 (m, 1H), 6.11 (m, 1H), 5.19 (s, 2H), 4.78 (m, 1H), 4.62 (s, 2H), 4.05 (t, 1H), 3.78 (dd, 1H), 3.70 (m, 3H), 3.60 (m, 1H), 2.86 (m, 2H), 2.02 (s, 3H); MS (ESI+) for C23H25N3O5 m/z 424 (M+H)+; [α]25D=−17° (c 0 77, DMSO).

후처리

  1. washThe mixture is then washed with H2O (2×15 mL) and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product is chromatographed on a Flash 40S silica gel (40 g, 32-63 μm) cartridge
  5. washeluting with a gradient of MeOH/CH2Cl2 (0.5/99.5-2/98)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8f79fd1ec183403780bef650daa2bed4
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06972286B2

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