Water → 2-(Tert-butyl)-5-(4-chlorobutyl)-3,5-dimethylimidazolidin-4-one

HRID 712815Notes

Reaction equation

HRID 712815 reaction equation
[C:1]([C@H:5]1[N:9]([CH3:10])[C:8](=[O:11])[C@:7]([CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])([CH3:12])[N:6]1C(OC(C)(C)C)=O)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+].O>C(Cl)Cl>[C:1]([CH:5]1[N:9]([CH3:10])[C:8](=[O:11])[C:7]([CH2:13][CH2:14][CH2:15][CH2:16][Cl:17])([CH3:12])[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 117966772(2S,5R)-tert-butyl 2-(tert-butyl)-5-(4-chlorobutyl)-3,5-dimethyl-4-oxoimidazolidine-1-carboxylate

Product 1

HCID 144639502-(Tert-butyl)-5-(4-chlorobutyl)-3,5-dimethylimidazolidin-4-oneYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled of (2S,5R)-tert-butyl 2-(tert-butyl)-5-(4-chlorobutyl)-3,5-dimethyl-4-oxoimidazolidine-1-carboxylate (D44) (465 mg, 1.28 mmol) in dry DCM (2 ml), TFA (1 ml, 12.8 mmol) was added and the solution stirred for 12 hrs at RT. The reaction mixture was treated with NaHCO3 sat sol with vigorous stirring until pH˜7. The resulting mixture was poured into water and the aqueous phase extracted with DCM (3×10 ml), dried over Na2SO4 and evaporated in vacuo to afford the title compound (D45) (310 mg).

Workup

  1. additionwas added
  2. stirringwith vigorous stirring until pH˜7
  3. extractionthe aqueous phase extracted with DCM (3×10 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c66d3f68e0834f94b0215b2d7a285883
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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