Triethylamine → HCID 131727051, compound

HRID 30296Notes

Reaction equation

HRID 30296 reaction equation
C(N(CC)CC)C.[CH2:8]1[NH:15][CH2:14][CH:13]2[CH:9]1[CH2:10][C:11]1[CH:18]=[CH:17][S:16][C:12]=12.Cl[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(Cl)Cl.[Cl-].[Na+].O>[CH2:23]([O:22][C:20]([N:15]1[CH2:14][CH:13]2[CH:9]([CH2:10][C:11]3[CH:18]=[CH:17][S:16][C:12]=32)[CH2:8]1)=[O:21])[CH3:24]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 597894331,2,3,3a,7,7a-Hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

Product 1

HCID 131727051HCID 131727051, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Triethylamine (741 mg, 7.32 mmol) was added to a solution of the product from step h) (493 mg, 2.44 mmol) in 12 mL of CH2Cl2 at ° C. followed by the addition of ethyl chloroformate (529 mg, 4.88 mmol). The reaction was allowed to come to room temperature and was stirred for two hours. The reaction mixture was diluted with brine (15 mL) and extracted with dichloromethane (3×15 mL). The combined organic extracts were dried with MgSO4 and the solvent was evaporated in vacuo give the crude product that was purified by column chromatography (SiO2) using a 0-30% ethyl acetate-hexane gradient to give the subtitle compound. MS calculated for C12H15NO2S+H: 238, observed: 238.

Workup

  1. customto come to room temperature
  2. extractionextracted with dichloromethane (3×15 mL)
  3. dry with materialThe combined organic extracts were dried with MgSO4
  4. customthe solvent was evaporated in vacuo
  5. customgive the crude product that
  6. customwas purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-056ac90560d6431bbd9b50aa1d53ffb7
Source dataset
uspto-grants-2008_09
Patent number
US07423056B2

Reaction notes

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