Triethylamine → HCID 86644168, compound

HRID 1523700Notes

Reaction equation

HRID 1523700 reaction equation
[OH:1][N:2]=[C:3]([Cl:12])[C@:4]1([CH3:11])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>CCOCC>[CH3:10][C:6]1([CH3:9])[O:5][C@:4]([CH3:11])([C:3]([Cl:12])=[N:2][O:1][S:14]([CH3:13])(=[O:16])=[O:15])[CH2:8][O:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86644167HCID 86644167, compound

Product 1

HCID 86644168HCID 86644168, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(S)—N-hydroxy-2,2,4-trimethyl-1,3-dioxolane-4-carbimidoyl chloride (5.5 g, 28.4 mmol) was dissolved in Et2O (150 mL) and methanesulfonyl chloride (2.21 ml, 28.4 mmol) was added. Triethylamine (3.96 ml, 28.4 mmol) was added dropwise and the reaction was stirred at ambient temperature for 1 hour. The resulting solids were filtered and the filtrate concentrated. The residue was purified over silica gel (100% CH2Cl2) to afford (S)-2,2,4-trimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (4.7 g, 17.3 mmol, 60.9% yield) as an amber oil.

Workup

  1. filtrationThe resulting solids were filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was purified over silica gel (100% CH2Cl2)

Sources & evidence

ORD record
ord-c6687531aed140afbb7e7fbb394d9921
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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