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

HRID 2112741노트

반응식

HRID 2112741 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.CO.C(OCC)C>[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

6

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 38.5%

시약·촉매·용매 2

HCID 13387N-methyl-2-pyrrolidone용매HCID 21864698Diethyl ether methanol용매

실험 절차

A mixture of 4-(acetylamino)-3-hydroxyphenyl acetate (669 mg, 3.2 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (748 mg, 2.9 mmol) and Cs2CO3 ((1.05 g, 3.2 mmol) in 1-methyl-pyrrolidinone (10 mL) was stirred at room temperature over night. The reaction mixture was partitioned between ethyl acetatwe and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give a yellow oil which was suspended in methanol/diethyl ether. The precipitate was filtered off and dried to give the sub-title compound (296 mg).

후처리

  1. customThe reaction mixture was partitioned between ethyl acetatwe and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil which
  6. filtrationThe precipitate was filtered off
  7. customdried

출처 및 근거

ORD 기록
ord-34e02ff61af84e5389eb2c50ab9fc451
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07524856B2

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