Triethylamine → HCID 57835390, compound

HRID 599710Notes

Reaction equation

HRID 599710 reaction equation
[CH2:1]([C:3]([C:16]1[CH:29]=[CH:28][C:19]([O:20][CH2:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[C:18]([CH3:30])[CH:17]=1)([C:6]1[S:10][C:9]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:8]=2[CH:7]=1)[CH2:4][CH3:5])[CH3:2].CCN(CC)CC.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:26][C:23]([CH3:25])([CH3:24])[C:22](=[O:27])[CH2:21][O:20][C:19]1[CH:28]=[CH:29][C:16]([C:3]([C:6]2[S:10][C:9]3[CH:11]=[CH:12][C:13]([O:15][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:14][C:8]=3[CH:7]=2)([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:17][C:18]=1[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57835418HCID 57835418, compound

Product 1

HCID 57835390HCID 57835390, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-{4-[1-ethyl-1-(5-hydroxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (260 mg, 0.612 mmol) in CH2Cl2 (20 mL) at RT is treated with Et3N (0.40 mL) and methanesulfonyl chloride (140 mg, 1.22 mmol). The mixture is stirred for 30 min and quenched with water (1.0 mL). The organic layer is concentrated and purified using silica gel column chromatography (25% EtOAc/Hex) to afford the title compound (190 mg, 62%).

Workup

  1. customquenched with water (1.0 mL)
  2. concentrationThe organic layer is concentrated
  3. custompurified

Sources & evidence

ORD record
ord-8628007dbcb1485982f71190fe973e1c
Source dataset
uspto-grants-2011_03
Patent number
US07897789B2

Reaction notes

Loading…