Triethylamine → HCID 18536039, compound

HRID 412150Notes

Reaction equation

HRID 412150 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].CCOC(C)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][S:32]([CH3:31])(=[O:34])=[O:33])[CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 18536035HCID 18536035, compound

Product 1

HCID 18536039HCID 18536039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude product from Step A (52.6 mmol) in 150 mL of dichloromethane at 0° C. was added triethylamine (14.66 mL, 105 mmol), followed by methanesulfonyl chloride (6.52 mL, 84.3 mmol). After 30 minutes, the reaction was poured into EtOAc and washed with water, saturated NH4Cl solution, saturated NaHCO3 solution, and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a white solid which was used without further purification.

Workup

  1. washwashed with water, saturated NH4Cl solution, saturated NaHCO3 solution, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was isolated as a white solid which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-61d16a77f0014137bef8cf825592c163
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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