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

HRID 515049Notes

Reaction equation

HRID 515049 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e70ca750300b4d5ebbc8257cfb96410f
Source dataset
uspto-grants-2015_08
Patent number
US09108948B2

Reaction notes

Loading…