Dimethyl Sulfoxide → HCID 57991852, compound

HRID 2075317Notes

Reaction equation

HRID 2075317 reaction equation
C(OC([C@@H:8]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([C:50]([F:53])([F:52])[F:51])=[CH:46][CH:45]=1)[CH2:9][N:10]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[C:11]1[S:15][C:14]([C:16]2[CH:17]=[CH:18][C:19]([N+:33]([O-:35])=[O:34])=[C:20]([CH:22](C(OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=2)=[N:13][N:12]=1)=O)(C)(C)C.[Cl-].[Li+].[OH2:56].CS(C)=O>[Cl-].[Na+].O.CCOC(C)=O>[C:39]([O:38][C:36]([N:10]([CH2:9][C@@H:8]([NH:10][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:56])[CH2:43][C:44]1[CH:45]=[CH:46][C:47]([C:50]([F:52])([F:53])[F:51])=[CH:48][CH:49]=1)[C:11]1[S:15][C:14]([C:16]2[CH:17]=[CH:18][C:19]([N+:33]([O-:35])=[O:34])=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:21]=2)=[N:13][N:12]=1)=[O:37])([CH3:41])([CH3:42])[CH3:40]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 433294Lithium Chloride2×HCID 67089473HCID 67089473, compound

Product 1

HCID 57991852HCID 57991852, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a 500 mL round bottom flask was added diethyl 2-(5-(5-((S)-2-(tert-butoxycarbonyl)-3-(4-(trifluoromethyl)phenyl)propyl-boc-amino)-1,3,4-thiadiazol-2-yl)-2-nitrophenyl)malonate (3.60 g, 4.60 mmol), lithium chloride (0.390 g, 9.21 mmol), distilled water (0.0830 g, 4.60 mmol) and 50 mL DMSO. The reaction mixture was heated to 100° C. and stirred at this temperature for 3 hours. LC-MS indicated the reaction was not complete. Another 4 equivalents of LiCl was added. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to ambient temperature, and 200 mL EtOAc and 200 mL brine were added. The organic portion was separated. The aqueous portion was extracted with EtOAc. The combined organic portions were washed with brine and dried over sodium sulfate. The crude mixture (3.40 g) was used in the following reaction without further purification.

Workup

  1. stirringThe reaction mixture was stirred at 100° C. overnight
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customThe organic portion was separated
  4. extractionThe aqueous portion was extracted with EtOAc
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe crude mixture (3.40 g) was used in the following reaction without further purification

Sources & evidence

ORD record
ord-8ed4125451c143a182b6a8b1e90d590a
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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