Cesium carbonate → 4-(acetylamino)-3-[(2S)-oxiran-2-ylmethoxy]phenyl acetate

HRID 270088ノート

反応式

HRID 270088 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([OH:15])[CH:6]=1)(=[O:3])[CH3:2].[N+](C1C=C(S(O[CH2:29][C@@H:30]2[CH2:32][O:31]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:14])[CH3:13])=[C:7]([O:15][CH2:29][C@@H:30]2[CH2:32][O:31]2)[CH:6]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 688181524-Acetamido-3-hydroxyphenyl acetate

生成物 1

HCID 715703414-(acetylamino)-3-[(2S)-oxiran-2-ylmethoxy]phenyl acetate収率 38%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

A solution of 4-(acetylamino)-3-hydroxyphenyl acetate (669 mg, 3.2 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (748 mg, 2.9 mol) and caesium carbonate (1.05 g, 3.2 mmol) in 1-methyl-pyrrolidinone (10 mL) was stirred over night at room temperature, and then partitioned between water and ethyl acetate. The organic phase was washed twice with water and concentrated to an yellow oil, which was suspended in methanol/diethyl ether, ½. The precipitated beige solid was filtered off and dried to give the titled compound (296 mg, 38%).

後処理

  1. custompartitioned between water and ethyl acetate
  2. washThe organic phase was washed twice with water
  3. concentrationconcentrated to an yellow oil, which
  4. filtrationThe precipitated beige solid was filtered off
  5. customdried

出典と根拠

ORDレコード
ord-ef6711d061bc446fb7709b68a6d153aa
出典データセット
uspto-grants-2008_11
特許番号
US07449475B2

反応ノート

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