Trifluoroacetic acid methylene chloride → HCID 131728810, compound

HRID 2080998Notes

Reaction equation

HRID 2080998 reaction equation
CC([C:5]1([C:20]([O-:22])=[O:21])[CH2:9][N:8]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:7](=[O:18])[N:6]1[CH3:19])(C)C.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24].C(Cl)Cl>>[OH:29][C:23]([C:25]([F:28])([F:27])[F:26])=[O:24].[CH3:19][N:6]1[CH:5]([C:20]([OH:22])=[O:21])[CH2:9][N:8]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[C:7]1=[O:18]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 131728811HCID 131728811, compound

Product 1

HCID 131728810HCID 131728810, compound

Procedure

To a stirred solution of 1,1-dimethylethyl 3-methyl-2-oxo-4-imidazolidinecarboxylate (1.0 g, 5 mmol) (prepared as described in step (iii) of Example 13) in N,N-dimethylformamide (20 ml) at 0° C. was added sodium hydride (60% dispersion in oil) (220 mg, 5.5 mmol). After 10 minutes a solution of 4-(2-chloroethyl)morpholine (898 mg, 6 mmol) in N,N-dimethylformamide (2 ml) and potassium iodide (166 mg, 1 mmol) was added and the mixture was heated at 70° C. for 2 hours. After cooling to room temperature water was added and the mixture was partitioned between saturated sodium hydrogen carbonate solution and dichloromethane. The organic extracts were separated, washed with water and brine, dried and evaporated. The residue was purified by silcia gel chromatography eluting with 5-10% 2M ammonia in methanol and dichloromethane to give 1,1-dimethylethyl-3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxylate (740 mg, 47%) as an oil. LC/MS [M+H]+=314. (ii) A solution of 1,1-dimethylethyl-3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxylate (740 mg, 2.361 mmol) in TFA/DCM (1:2, 6 ml) was stirred at room temperature for 5 hours. The solution was evaporated and the residue was co-evaporated with DCM and dried to give crude 3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxylic acid TFA salt (assume ˜2.3 mmol) which was used in the next step. LC/MS [M+H]+=258.

Workup

  1. customThe solution was evaporated
  2. customdried

Sources & evidence

ORD record
ord-a83dbcaf950d4ca9a029ad360d17baea
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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