Hydrochloric Acid → tert-Butyl {2-(2-oxoimidazolidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

HRID 220654Notes

Reaction equation

HRID 220654 reaction equation
[NH2:1][CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1.Br[CH2:23][CH2:24][N:25]=[C:26]=[O:27].[H-].[Na+].Cl>ClCCl>[O:27]=[C:26]1[NH:25][CH2:24][CH2:23][N:1]1[CH2:2][CH:3]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 42559572-Bromoethyl isocyanateHCID 43094068tert-butyl N-{2-amino-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Product 1

HCID 59536914tert-Butyl {2-(2-oxoimidazolidin-1-yl)-1-[3-(trifluoromethyl)phenyl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cooled solution of 302 mg (0.99 mmol) of the compound from Example 101A in 10 ml of dichloromethane was admixed dropwise with 99 μl (1.09 mmol) of 2-bromoethyl isocyanate. After 10 minutes, the ice bath was removed and the mixture was stirred for a further 5 min. All of the volatile components were removed on a rotary evaporator. The residue was taken up in 5 ml of anhydrous THF and admixed, with ice cooling, with 44 mg of sodium hydride (60% in mineral oil, 1.09 mmol). After 2 h, 1 ml of 1M hydrochloric acid was added and the reaction mixture was freed from the solvent on a rotary evaporator. The aqueous residue was dissolved in DMSO and purified by preparative HPLC [Method 23]. The product fraction was freed from the solvents on a rotary evaporator. Drying of the residue in an HV gave 210 mg (38% of theory) of the title compound.

Workup

  1. customthe ice bath was removed
  2. customAll of the volatile components were removed on a rotary evaporator
  3. waitAfter 2 h
  4. customthe reaction mixture was freed from the solvent on a rotary evaporator
  5. dissolutionThe aqueous residue was dissolved in DMSO
  6. custompurified by preparative HPLC [Method 23]
  7. customThe product fraction was freed from the solvents on a rotary evaporator
  8. customDrying of the residue in an HV

Sources & evidence

ORD record
ord-1284d63745a8402ab7220b3705405d53
Source dataset
uspto-grants-2012_06
Patent number
US08202895B2

Reaction notes

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