Hydrochloric Acid → HCID 69351593, compound

HRID 496249Notes

Reaction equation

HRID 496249 reaction equation
C([N:8]1[CH2:16][C:15](=[O:17])[C:14]([CH2:21][CH:22]=[CH2:23])([CH2:18][CH:19]=[CH2:20])[C@H:9]1[C:10]([O:12]C)=[O:11])(OC(C)(C)C)=O.[Li+].[OH-].Cl>O.CO>[CH2:21]([C:14]1([CH2:18][CH:19]=[CH2:20])[C:15](=[O:17])[CH2:16][NH:8][C@@H:9]1[C:10]([OH:12])=[O:11])[CH:22]=[CH2:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69898152HCID 69898152, compound

Product 1

HCID 69351593HCID 69351593, compoundYield 187.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.099 g of N-(BOC)-3,3-diallyl-4-oxo-(L)-proline, methyl ester in 0.4 mL of water and 1.6 mL of MeOH was added 25.7 mg of LiOH.monohydrate. The reaction mixture was sonicated for 2 h. The mixture was acidified with 1.2N HCl to pH=2 and concentrated in vacuo. The residue was treated with 1.5 mL of HCl/dioxane solution for 1.5 h. After concentration in vacuo, 0.12 g of 3,3-diallyl-4-oxo-(L)-proline was obtained which was used in the next step without purification.

Workup

  1. customThe reaction mixture was sonicated for 2 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with 1.5 mL of HCl/dioxane solution for 1.5 h
  4. concentrationAfter concentration in vacuo

Sources & evidence

ORD record
ord-1fb51e3d63b54501af9dcf926e26a804
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Reaction notes

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