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Hydrochloric Acid → tert-Butyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbonyl)methylamino]acetate

HRID 17493
ノート
印刷プレビュー

反応式

HRID 17493 の反応式
C[Al](C)C.Cl.[C:6]([O:10][C:11](=[O:15])[CH2:12][NH:13][CH3:14])([CH3:9])([CH3:8])[CH3:7].[C:16]([C:18]1[C:23]2[N:24]=[C:25]([C:27](OCC)=[O:28])[O:26][C:22]=2[C:21]([F:32])=[C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:19]=1[CH3:39])#[N:17].Cl>ClCCl>[C:16]([C:18]1[C:23]2[N:24]=[C:25]([C:27]([CH2:14][NH:13][CH2:12][C:11]([O:10][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:15])=[O:28])[O:26][C:22]=2[C:21]([F:32])=[C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:19]=1[CH3:39])#[N:17]
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 313Hydrochloric AcidHCID 11252350Sarcosine t-butyl ester hydrochlorideHCID 16682925TrimethylaluminumHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

生成物 1

HCID 86630857tert-Butyl [(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carbonyl)methylamino]acetate収率 87.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Under nitrogen atmosphere, trimethylaluminium (1.03 M n-hexane solution, 4.50 ml, 4.63 mmol) was dropwise added at room temperature to a dichloromethane (6 ml) solution of N-methylglycine tert-butyl ester hydrochloride (840 mg, 4.63 mmol), followed by stirring for 25 hours. Subsequently, a dichloromethane (4 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (500 mg, 1.54 mmol) was dropwise added, followed by stirring for 23 hours. After the reaction, aqueous 1 N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended and washed in diethyl ether to obtain the entitled compound (569 mg, 87%) as a white solid.

後処理

  1. stirringby stirring for 23 hours
  2. additionwas added to the reaction liquid
  3. temperaturewith cooling with ice
  4. stirringby stirring at room temperature
  5. customthe reaction liquid
  6. extractionwas extracted with chloroform
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. washwashed in diethyl ether

出典と根拠

ORDレコード
ord-abec07b406974cb0a332db3ca8eef204
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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