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Sodium Iodide → HCID 11331321、化合物

HRID 915288
ノート
印刷プレビュー

反応式

HRID 915288 の反応式
Cl[CH2:2][O:3][C:4](=[O:31])[N:5]([C:28](=[O:30])[CH3:29])[CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]3)=[C:15]([F:27])[CH:14]=2)[CH2:8]1.[I-].[Na+].[Cs].[C:35]([N:42]1[CH2:50][CH2:49][CH:45]([C:46]([OH:48])=[O:47])[CH2:44][CH2:43]1)([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>C(#N)C>[C:38]([O:37][C:35]([N:42]1[CH2:50][CH2:49][CH:45]([C:46]([O:48][CH2:2][O:3][C:4](=[O:31])[N:5]([C:28](=[O:30])[CH3:29])[CH2:6][C@@H:7]2[O:11][C:10](=[O:12])[N:9]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][S:22](=[O:26])(=[O:25])[CH2:21][CH2:20]4)=[C:15]([F:27])[CH:14]=3)[CH2:8]2)=[O:47])[CH2:44][CH2:43]1)=[O:36])([CH3:41])([CH3:39])[CH3:40]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 5354618CesiumHCID 58958555HCID 58958555、化合物

生成物 1

HCID 11331321HCID 11331321、化合物収率 72%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To (R)-acetyl-{3-[4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-carbamic acid chloromethyl ester (10) (751.8 mg, 1.58 mmol) and sodium iodide (236.0 mg, 1.58 mmol) in acetonitrile (30 mL), is added the cesium salt of N-BOC-isonipecotic acid (884.2 mg, 2.45 mmol). The mixture is heated to reflux overnight. After cooling to RT, the mixture is filtered and washed with dichloromethane. The filtrate is diluted with CH2Cl2 and water and the layers are separated. The aq layer is extracted with dichloromethane twice and the combined organic layers are washed with water, brine, dried over sodium sulfate and conc in vacuo. Purification by silica gel chromatography gave the title compound in 72% yield (757.3 mg, 1.13 mmol). 1H NMR (400 MHz, CDCl3): δ 7.47 (dd, 1H), 7.24 (t, 1H), 7.14 (dd, 1H), 5.88 (s, 2H), 4.78-4.85 (m, 1H), 4.18 (dd, 1H), 4.08 (t, 2H), 4.03 (dd, 2H), 3.67 (dd, 1H), 3.13-3.20 (m, 4H), 3.10 (dt, 1H), 2.83 (t, 2H), 2.60 (tt, 1H), 2.59 (s, 3H), 2.35-2.46 (m, 2H), 2.17-2.23 (m, 2H), 1.90-1.96 (m, 2H), 1.57-1.686 (m, 2H) 1.45 (s, 9H). MS-APCI (m/z+): 570.

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux overnight
  3. filtrationthe mixture is filtered
  4. washwashed with dichloromethane
  5. additionThe filtrate is diluted with CH2Cl2 and water
  6. customthe layers are separated
  7. extractionThe aq layer is extracted with dichloromethane twice
  8. washthe combined organic layers are washed with water, brine
  9. dry with materialdried over sodium sulfate and conc in vacuo
  10. customPurification by silica gel chromatography

出典と根拠

ORDレコード
ord-2264161bb69e4f4ba47f5eee1133f0ec
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265140B2

反応ノート

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