Triethylamine → HCID 86644165, compound

HRID 1511150Notes

Reaction equation

HRID 1511150 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 86644164HCID 86644164, compound

Product 1

HCID 86644165HCID 86644165, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(R)-N-hydroxy-2,2,4-trimethyl-1,3-dioxolane-4-carbimidoyl chloride (6.4 g, 33.1 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 stirred at ambient temperature for 1 hour. The resulting solids were filtered and the filtrate was concentrated. The residue was purified over silica gel (100% CH2Cl2) to afford (R)-2,2,4-trimethyl-N-(methylsulfonyloxy)-1,3-dioxolane-4-carbimidoyl chloride (5.8 g, 21.3 mmol, 64.6% yield) as an amber oil.

Workup

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

Sources & evidence

ORD record
ord-4f95530afe1042f981b81e6b821b09c6
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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