Water → Methanesulfonic acid, 2-[(1R,2S)-2-(4'-cyano-biphenyl-4-yl)-cyclopropyl]-ethyl ester

HRID 73301노트

반응식

HRID 73301 반응식
[OH:1][CH2:2][CH2:3][C@H:4]1[CH2:6][C@@H:5]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C.O>ClCCl>[CH3:21][S:22]([O:1][CH2:2][CH2:3][C@H:4]1[CH2:6][C@@H:5]1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:24])=[O:23]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 684076744'-[(1S,2R)-2-(2-Hydroxyethyl)cycloprop-1-yl]biphenyl-4-carbonitrile

생성물 1

HCID 86618016Methanesulfonic acid, 2-[(1R,2S)-2-(4'-cyano-biphenyl-4-yl)-cyclopropyl]-ethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of the product of Example 28F (4′-[(1S,2R)-2-(2-hydroxyethyl)cycloprop-1 yl]biphenyl-4-carbonitrile) and methanesulfonyl chloride (1.2 equivalents) in dichloromethane under N2 was added triethylamine (1.4 equivalents) at 0° C. The mixture was stirred at room temperature overnight, and then the mixture was treated with H2O. The separated organic layer was washed with brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the resulting residue was purified by chromatography on silica gel eluted with 4:1 hexanes/ethyl acetate to provide the title compound.

후처리

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe resulting residue was purified by chromatography on silica gel
  6. washeluted with 4:1 hexanes/ethyl acetate

출처 및 근거

ORD 기록
ord-439fff2291624451a43724511de73b2c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829041B2

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