Methanesulfonyl chloride → HCID 58392718, compound

HRID 446841Notes

Reaction equation

HRID 446841 reaction equation
[CH:1]([O:3][C:4]([N:6]1[CH2:30][C@:29]2([C:31](=[O:34])[CH2:32][OH:33])[C@@H:8]([CH2:9][C@H:10]3[C@H:23]4[C@@:14]([F:27])([C@:15]5([CH3:26])[C:20]([C@@H:21]([F:24])[CH2:22]4)=[CH:19][C:18](=[O:25])[CH:17]=[CH:16]5)[C@@H:13]([OH:28])[CH2:12][C@@:11]32[CH3:35])[CH2:7]1)=[O:5])=[CH2:2].[CH3:36][S:37](Cl)(=[O:39])=[O:38].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:1]([O:3][C:4]([N:6]1[CH2:30][C@:29]2([C:31](=[O:34])[CH2:32][O:33][S:37]([CH3:36])(=[O:39])=[O:38])[C@@H:8]([CH2:9][C@H:10]3[C@H:23]4[C@@:14]([F:27])([C@:15]5([CH3:26])[C:20]([C@@H:21]([F:24])[CH2:22]4)=[CH:19][C:18](=[O:25])[CH:17]=[CH:16]5)[C@@H:13]([OH:28])[CH2:12][C@@:11]32[CH3:35])[CH2:7]1)=[O:5])=[CH2:2]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58392688HCID 58392688, compound

Product 1

HCID 58392718HCID 58392718, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 164 (840 mg, 1.709 mmol), methansulfonyl chloride (160 μA, 2.051 mmol) and DIPEA (448 μl, 2.56 mmol) in DCM is stirred at RT under nitrogen overnight. The solution is partitioned between DCM and water, then the aqueous phase is extracted with DCM. The combined organic phases are washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give the title compound (774 mg, 80% yield).

Workup

  1. customThe solution is partitioned between DCM and water
  2. extractionthe aqueous phase is extracted with DCM
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent is evaporated

Sources & evidence

ORD record
ord-2252ffbd0c17416384516fcc05518401
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

Loading…