Triethylamine → 1-methanesulphonyloxy-3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butane

HRID 844588Notes

Reaction equation

HRID 844588 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[C:19]([C:21]2[C:22]3[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=3[CH:28]=[CH:29][CH:30]=2)=[O:20])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[CH3:38][S:39]([O:12][CH2:11][CH2:10][C@@H:9]([C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)[CH2:13][N:14]1[CH:18]=[CH:17][N:16]=[C:15]1[C:19]([C:21]1[C:22]2[CH2:23][CH2:24][CH2:25][CH2:26][C:27]=2[CH:28]=[CH:29][CH:30]=1)=[O:20])(=[O:41])=[O:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 540642943(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-ol

Product 1

HCID 598865681-methanesulphonyloxy-3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butaneYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3(S)-(3,4-Dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butan-1-ol (0.68 g) (see Preparation 103) and triethylamine (0.22 g) were dissolved in dichloromethane (15 ml), the solution cooled in an ice-bath and methanesulphonyl chloride (0.22 g) added. The mixture was stirred for 4 hours before removal of the solvent under reduced pressure to give a residue which was partitioned between ethyl acetate and water. The organic phase was separated and washed with saturated aqueous sodium hydrogen carbonate solution before being dried over anhydrous sodium sulphate. The solvent was removed under reduced pressure to give 1-methanesulphonyloxy-3(S)-(3,4-dichlorophenyl)-4-[2-(1,2,3,4-tetrahydro-5-naphthoyl)imidazol-1-yl]butane (0.82 g) as an oil.

Workup

  1. temperaturethe solution cooled in an ice-bath
  2. customto give a residue which
  3. customwas partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialbefore being dried over anhydrous sodium sulphate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-256beb8d7a5d413e9456bebaf962db7a
Source dataset
uspto-grants-2002_04
Patent number
US06380396B1

Reaction notes

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