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

HRID 270088노트

반응식

HRID 270088 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-ef6711d061bc446fb7709b68a6d153aa
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

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