Diisopropylethylamine → HCID 18940884, compound

HRID 356012Notes

Reaction equation

HRID 356012 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([SH:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:14]([O:16][CH:17]([O:27][CH2:28][CH3:29])[CH2:18]OS(C(F)(F)F)(=O)=O)[CH3:15].C(N(C(C)C)CC)(C)C.FC(F)(F)S([O-])(=O)=O>ClCCl.CCN(C(C)C)C(C)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([S:13][CH2:18][CH:17]([O:27][CH2:28][CH3:29])[O:16][CH2:14][CH3:15])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2758875TrifluoromethanesulfonateHCID 10535785HCID 10535785, compoundHCID 53910773HCID 53910773, compound

Product 1

HCID 18940884HCID 18940884, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of thiol (D3, 3.38 g, 17.5 mmol), acetal trifluoromethanesulphonate (D4, 5.05 g, 19 mmol) and diisopropylethylamine (3.2 ml, 19 mmol) in dry dichloromethane (80 ml) was stirred for 4.5 h at room temperature. Further small portions of trifluoromethane sulphonate and of DIPEA (2 drops each) were added and stirring was continued for another 1 h before the mixture was washed sequentially with dilute hydrochloric acid, dilute sodium hydroxide, and water. The organic phase was dried and evaporated, and the residue was chromatographed on silica (300 g) eluted with ethyl acetate to give the title compound (4.14 g, 76.6%), as a waxy solid, mp <52° C.

Workup

  1. stirringstirring
  2. waitwas continued for another 1 h before the mixture
  3. washwas washed sequentially with dilute hydrochloric acid, dilute sodium hydroxide, and water
  4. customThe organic phase was dried
  5. customevaporated
  6. customthe residue was chromatographed on silica (300 g)
  7. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-869b9183f02c4c60aa1e87c9f9f30fed
Source dataset
uspto-grants-1998_11
Patent number
US05834494

Reaction notes

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