Triethylamine → HCID 18536042, compound

HRID 412180Notes

Reaction equation

HRID 412180 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([OH:26])[CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][S:35]([CH3:34])(=[O:37])=[O:36])[CH:24]=3)[CH:19]=[CH:18][CH:17]=2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18536029HCID 18536029, compound

Product 1

HCID 18536042HCID 18536042, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step E (426 mg, 1.19 mmol) in 5 mL of DMF at 0° C. was added triethylamine (0.532 mL, 3.82 mmol), followed by methanesulfonyl chloride (0.212 mL, 2.73 mmol). The reaction was stirred at room temperature overnight, then partitioned between EtOAc and 50% NaHCO3 solution. The organic layer was washed with water and brine, dried (MgSO4), filtered, and concentrated in vacuo. The product was isolated as a yellow gum which was used without further purification.

Workup

  1. custompartitioned between EtOAc and 50% NaHCO3 solution
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe product was isolated as a yellow gum which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-adbfa7bb62424b56a2b35b33ea4ebf48
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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