Water → HCID 57524699, compound

HRID 1477828Notes

Reaction equation

HRID 1477828 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(OC([NH:13][C:14]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:15]=1[CH:16]=[CH:17][N:18]2[CH:23]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25])=O)(C)(C)C.C(N(CC)CC)C.O>C(Cl)Cl>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([CH:23]([N:18]2[C:19]3[C:15](=[C:14]([NH:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH:22]=[CH:21][CH:20]=3)[CH:16]=[CH:17]2)[C:24]([O:26][CH3:27])=[O:25])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70565186HCID 70565186, compound

Product 1

HCID 57524699HCID 57524699, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (159 μL, 2.04 mmol) was added to a stirred solution of 2b (320 mg, 1.02 mmol) and triethylamine (213 μL, 1.53 mmol) in DCM (3 mL) at rt. After 1 h, the reaction mixture was poured into water and extracted with DCM. The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier), followed by lyophilization of the purified fractions to afford the title compound 17. m/z (ES) 393 (MH)+ IP=C rating.

Workup

  1. extractionextracted with DCM
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (CH3CN/H2O as eluent, 0.05% TFA as modifier)

Sources & evidence

ORD record
ord-73bf0be6295b4e408ce935f9163938d7
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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