Methanesulfonyl chloride → HCID 86622506, compound

HRID 2261438Notes

Reaction equation

HRID 2261438 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([C:15]2[S:22][C:21]([CH3:23])=[C:20]3[C:16]=2[CH2:17][C@H:18]2[C:24]([CH3:26])([CH3:25])[C@H:19]23)=[O:14])=[CH:7][CH:6]=1.CCN(C(C)C)C(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[O:14]=[C:13]([C:15]1[S:22][C:21]([CH3:23])=[C:20]2[C:16]=1[CH2:17][C@H:18]1[C:24]([CH3:26])([CH3:25])[C@H:19]12)[CH2:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][CH2:3][CH2:2][O:1][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 59380606HCID 59380606, compound

Product 1

HCID 86622506HCID 86622506, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-[4-(3-hydroxy-propyl)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (147 mg, 0.40 mmol), DIPEA (0.11 mL, 0.642 mmol) in DCM (5 mL) is treated with methane sulfonylchloride (40 μL, 0.481 mmol) at 0° C. The solution is stirred at 0° C. for 30 min, then at rt for 1 h before it is diluted with DCM and washed with 0.1 N aq. NaOH solution, followed by 10% aq. citric acid solution. The organic layer is separated, dried over Na2SO4 and evaporated to give methanesulfonic acid 3-{4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenyl}-propyl ester (176 mg) as a colourless oil; LC-MS: tR=1.14 min, [M+1]+=447.25.

Workup

  1. washwashed with 0.1 N aq. NaOH solution
  2. customThe organic layer is separated
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-aef171b5a17148268f23680ffedd9c79
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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