Pyridine → HCID 69734019、化合物

HRID 488357ノート

反応式

HRID 488357 の反応式
[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]

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 69733820HCID 69733820、化合物

生成物 1

HCID 69734019HCID 69734019、化合物収率 93.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8f79fd1ec183403780bef650daa2bed4
出典データセット
uspto-grants-2005_12
特許番号
US06972286B2

反応ノート

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