Lithium Hydroxide → Lithium 4-benzyl-2,5-dioxo-1-[(1R)-1-phenylethyl]imidazolidine-4-carboxylate

HRID 717317Notes

Reaction equation

HRID 717317 reaction equation
C([O:3][C:4](=[O:30])[C:5]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([NH:11][C:12](=[O:22])[NH:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])[C:6]([O:8]CC)=O)C.[OH-].[Li+:32]>O1CCCC1.CO>[CH2:23]([C:5]1([C:4]([O-:3])=[O:30])[C:6](=[O:8])[N:13]([C@@H:14]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:15])[C:12](=[O:22])[NH:11]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1.[Li+:32]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 89508911Diethylbenzyl({[(1R)-1-phenylethyl]carbamoyl}amino)propanedioate

Product 1

HCID 90386932Lithium 4-benzyl-2,5-dioxo-1-[(1R)-1-phenylethyl]imidazolidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step C (7.8 g, 18.91 mmol) in tetrahydrofuran (60 mL) and methanol (20.00 mL) was added a 1 M lithium hydroxide solution (19.86 mL, 19.86 mmol) and the mixture stirred for 30 min. The solvent was removed in vacuo and the residue azeotroped with toluene (3×25 mL) to afford the title compound as a colorless amorphous solid. LC/MS 339.1 (M+1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue azeotroped with toluene (3×25 mL)

Sources & evidence

ORD record
ord-7ceea42958fc4dd29d6a10fe2f27d214
Source dataset
uspto-grants-2015_11
Patent number
US09193717B2

Reaction notes

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