1,1-Dimethylethyl 3-methyl-2-oxo-4-imidazolidinecarboxylate → 3-Methyl-2-oxoimidazolidine-4-carboxylic acid

HRID 2080987Notes

Reaction equation

HRID 2080987 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]([O:9]C(C)(C)C)=[O:8])[CH2:5][NH:4][C:3]1=[O:14]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:1][N:2]1[CH:6]([C:7]([OH:9])=[O:8])[CH2:5][NH:4][C:3]1=[O:14]

Participants

3

Reactant 1

HCID 671035641,1-Dimethylethyl 3-methyl-2-oxo-4-imidazolidinecarboxylate

Product 1

HCID 553001513-Methyl-2-oxoimidazolidine-4-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-dimethylethyl 3-methyl-2-oxo-4-imidazolidinecarboxylate (801 mg, 4 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4-imidazolidinecarboxylic acid) in TFA/DCM (trifluoroacetic acid/dichloromethane) (1:2, 9 ml) was stirred at room temperature for 6 hours. The solution was evaporated, the residue was co-evaporated with toluene and dried to give crude 3-methyl-2-oxo-4-imidazolidinecarboxylic acid (assume ˜4 mmol) which was used in the next step. LC/MS [M+H]+=145.

Workup

  1. customThe solution was evaporated
  2. customdried

Sources & evidence

ORD record
ord-a5cdd4b841764d97978ab46e88098be3
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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