Methanesulfonyl chloride → HCID 58392711, compound

HRID 446848Notes

Reaction equation

HRID 446848 reaction equation
[CH:1]([O:3][C:4]([N:6]1[CH2:30][C@:29]2([C:31](=[O:34])[CH2:32]O)[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)=O.CCN(C(C)C)C(C)C.C([S-])C.[Na+]>CN(C=O)C>[CH:1]([O:3][C:4]([N:6]1[CH2:30][C@:29]2([C:31](=[O:34])[CH2:32][S:37][CH3:36])[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

6

Reactant 4

HCID 31297Methanesulfonyl chloride2×HCID 81531Diisopropylethylamine2×HCID 4459711Sodium ethanethiolateHCID 58392688HCID 58392688, compound

Product 1

HCID 58392711HCID 58392711, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 164 (203 mg, 0.413 mmol), methansulfonyl chloride (38.6 μl, 0.496 mmol) and DIPEA (108 μl, 0.620 mmol) in dry DMF (3 ml) is stirred at RT under nitrogen for 1 hour. Further methansulfonyl chloride (16.09 μl, 0.207 mmol) and DIPEA (54.1 μl, 0.310 mmol) are added and the mixture is stirred at RT for 2 hours. Sodiumethanethiolate (87 mg, 1.239 mmol) is added and the mixture is stirred at RT for 16 hours. The reaction the mixture is partitioned between AcOEt and brine, then the aqueous phase is extracted with AcOEt and the combined organic layers are washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give a oil which is purified by silica gel chromatography (eluent: AcOEt/petroleum ether 2/3) to afford the title compound (118 mg, 0.226 mmol, 54.8% yield).

Workup

  1. stirringthe mixture is stirred at RT for 2 hours
  2. stirringthe mixture is stirred at RT for 16 hours
  3. customThe reaction the mixture
  4. customis partitioned between AcOEt and brine
  5. extractionthe aqueous phase is extracted with AcOEt
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customThe solvent is evaporated
  10. customto give a oil which
  11. customis purified by silica gel chromatography (eluent: AcOEt/petroleum ether 2/3)

Sources & evidence

ORD record
ord-89450dd0415642d180ca5b84f9f28b38
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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