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

HRID 515049ノート

反応式

HRID 515049 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e70ca750300b4d5ebbc8257cfb96410f
出典データセット
uspto-grants-2015_08
特許番号
US09108948B2

反応ノート

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