Dimethyl Sulfoxide → [tert-Butoxycarbonyl-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-amino]-acetic Acid Methyl Ester

HRID 902707Notes

Reaction equation

HRID 902707 reaction equation
[H-].[Na+].CS(C)=O.[C:7]([O:11][C:12](=[O:51])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[C:41]=2[Cl:50])[CH2:25][CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:15]=1)([CH3:10])([CH3:9])[CH3:8].[CH3:52][O:53][C:54](=[O:57])[CH2:55]Br>CN(C=O)C>[CH3:52][O:53][C:54](=[O:57])[CH2:55][N:13]([C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:51])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH2:21][CH2:22][CH2:23][N:24]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:48])([F:49])[F:47])[C:41]=2[Cl:50])[CH2:25][CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10175511(3-{3-[(2-Chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 69780857[tert-Butoxycarbonyl-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-amino]-acetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of sodium hydride (18.8 mg, 0.47 mmol, 60% in mineral oil) in anhydrous DMF (10 mL) at 0° C. and DMSO (10 ml) was added dropwise a solution of (3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-carbamic acid tert-butyl ester (150 mg, 0.235 mmol) in DMF (5 ml). The solution was stirred at 0° C. for 20 minutes and was then treated with bromo-acetic acid methyl ester (72 mg 0.47 mmol). The resulting solution was warmed to room temperature and stirred for 6 hours. The reaction mixture was poured into ice water (30 ml). The mixture was extracted with EtOAC (3×) and the combine organic layers were washed with saturated aqueous sodium bicarbonate (2×), brine (×), dried over sodium sulphate, and filtered. The ethyl acetate filtrate was concentrated to afford the title compound as an oil. MS(ES) m/e 711.2 (M+).

Workup

  1. temperatureThe resulting solution was warmed to room temperature
  2. stirringstirred for 6 hours
  3. extractionThe mixture was extracted with EtOAC (3×)
  4. washthe combine organic layers were washed with saturated aqueous sodium bicarbonate (2×), brine (×)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationThe ethyl acetate filtrate was concentrated

Sources & evidence

ORD record
ord-88e6e48e68fa4940bced816ccb734255
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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