Methanesulfonyl chloride → HCID 86622512, compound

HRID 2261456Notes

Reaction equation

HRID 2261456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][CH2:16][C:17]([C:19]2[S:26][C:25]([CH3:27])=[C:24]3[C:20]=2[CH2:21][C@H:22]2[C:28]([CH3:30])([CH3:29])[C@H:23]23)=[O:18])[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][OH:12].CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][CH2:16][C:17](=[O:18])[C:19]2[S:26][C:25]([CH3:27])=[C:24]3[C:20]=2[CH2:21][C@H:22]2[C:28]([CH3:30])([CH3:29])[C@H:23]23)[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][S:41]([CH3:40])(=[O:43])=[O:42]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 67415421HCID 67415421, compound

Product 1

HCID 86622512HCID 86622512, compoundYield 471.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[3-chloro-4-(3-hydroxy-propoxy)-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (430 mg, 0.958 mmol) in DCM (20 mL) and DIPEA (0.262 mL, 1.53 mmol) is added methane sulfonylchloride (0.090 mL, 1.15 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 30 min. The reaction mixture is diluted with DCM, washed with 0.1 N aq. NaOH followed by 10% aq. citric acid solution, dried over MgSO4 and evaporated to give methanesulfonic acid 3-{2-chloro-6-methoxy-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenoxy}-propyl ester (2.38 g) as a brown oil; LC-MS: tR=1.14 min, [M+1]+=527.23.

Workup

  1. washwashed with 0.1 N aq. NaOH
  2. dry with materialdried over MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-2acceacf519b43619b31b33cf90fa60f
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

Loading…