Diethyl Oxalate → HCID 54692279, compound

HRID 1162827Notes

Reaction equation

HRID 1162827 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:13](=[O:25])[CH2:12]2)=[S:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[C:41](OCC)(=[O:47])[C:42](OCC)=[O:43]>CN(C=O)C.CO.C1(C)C=CC=CC=1>[CH:1]1([CH2:7][N:8]2[C:42](=[O:43])[C:41]([OH:47])=[C:12]3[C:13](=[O:25])[N:14]([CH2:17][C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=4)[CH2:15][CH2:16][N:11]3[C:9]2=[S:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 7268Diethyl OxalateHCID 8028Tetrahydrofuran2×HCID 2733832Lithium Hexamethyldisilazide2×HCID 86617476HCID 86617476, compound

Product 1

HCID 54692279HCID 54692279, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N-(Cyclohexylmethyl)-4-(4-fluorobenzyl)-3-oxopiperazine-1-carbothioamide (239 mg, 0.66 mmol) was azeotroped with anhydrous toluene and dissolved in anhydrous DMF (2 mL). The solution was cooled to 0° C., and a 1.0 M solution of lithium bis(trimethylsilyl)amide in THF (789 μL, 0.79 mmol) and diethyl oxalate (134 μL, 0.99 mmol) were added sequentially. After 15 min, the reaction was warmed to ambient temperature and treated once more with 1.0 M lithium bis(trimethylsilyl)amide in THF (789 μL, 0.79 mmol). The dark orange solution was stirred for 18 h. THF was removed by warming the reaction under a nitrogen stream, and the residue was diluted with MeOH. The resulting precipitate was collected by filtration and washed with MeOH to afford the title compound as a pale yellow solid.

Workup

  1. temperaturethe reaction was warmed to ambient temperature
  2. customTHF was removed
  3. temperatureby warming
  4. customthe reaction under a nitrogen stream
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with MeOH

Sources & evidence

ORD record
ord-bc109324a587436f81ef4d4c6db77791
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

Loading…