Sodium hydride → HCID 58671550、化合物

HRID 2221095

反応式

HRID 2221095 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]([NH:13][CH:14](P(OCC)(OCC)=O)[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:27]([C:29]1[CH:34]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[N:32]=[CH:31][C:30]=1[NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=O>C1COCC1>[CH2:3]([O:10][C:11]([NH:13]/[C:14](=[CH:27]\[C:29]1[C:30]([NH:41][C:42]([O:43][C:44]([CH3:47])([CH3:45])[CH3:46])=[O:48])=[CH:31][N:32]=[C:33]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:34]=1)/[C:15]([O:17][CH3:18])=[O:16])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 11068333Methyl 2-(((benzyloxy)carbonyl)amino)-2-(diethyl phosphono)acetateHCID 58671548HCID 58671548、化合物

生成物 1

HCID 58671550HCID 58671550、化合物収率 42%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a slurry of 60% of sodium hydride (228 mg, 5.7 mmol) in THF (17 mL) at 0° C. was added 1A (1.88 g, 5.24 mmol) in several portions over 10 min. The reaction mixture was then brought to RT for 20 min, then cooled again at 0° C. A suspension of 3C (1.42 g, 4.76 mmol) in THF (17 mL) was added over 10 min at 0C, then the reaction was warmed up to RT. After stirring for 20 min, the reaction was quenched with water (40 mL). The aqueous layer was extracted with EtOAc (50 mL×2). The combined EtOAc extracts were dried (Na2SO4), filtered and concentrated. The resulting residue was purified by silica gel (110 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give the title compound as an off-white solid (1 g, 42%). LC/MS (method A): retention time=3.33 min, (M+H)+=504.

後処理

  1. temperaturethe reaction was warmed up to RT
  2. customthe reaction was quenched with water (40 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  4. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel (110 g) column chromatography
  8. washeluting with a gradient of EtOAc (0-60%) in hexane

出典と根拠

ORDレコード
ord-cb1e9c6501204994b1b53696e03a67be
出典データセット
uspto-grants-2008_05
特許番号
US07368458B2

関連ノート

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