Chloroacetyl chloride → HCID 23144494, compound

HRID 337456Notes

Reaction equation

HRID 337456 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[S:13][C:12]([NH2:14])=[N:11][C:10]=1[C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)=[O:8].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].C(=O)([O-])O.[Na+]>C1COCC1.O>[Cl:27][CH2:28][C:29]([NH:14][C:12]1[S:13][C:9]([C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:8])=[C:10]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:11]=1)=[O:30]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chloride2×HCID 8471Triethylamine2×HCID 516892Sodium BicarbonateHCID 23144251HCID 23144251, compound

Product 1

HCID 23144494HCID 23144494, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 186 (0.900 g, 2.42 mmol) was dissolved in THF (10 mL), and N,N-dimethylaminopyridine (29.6 mg, 0.242 mmol), triethylamine (0.740 mL, 5.32 mmol) and chloroacetyl chloride (0.390 mL, 4.84 mmol) were added thereto under ice-cooling, followed by stirring at room temperature for 2 hours. Further, triethylamine (0.740 mL, 5.32 mmol) and chloroacetyl chloride (0.390 mL, 4.84 mmol) were added to the reaction mixture under ice-cooling, followed by stirring for 1 hour at room temperature. Water and a saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture, and the precipitated solid was collected by filtration. The resulting solid was purified through silica gel column chromatography (hexane:ethyl acetate=2:1) to afford the entitled Compound 262 (0.810 g, 96%) as pale yellow crystals.

Workup

  1. temperatureunder ice-cooling
  2. temperaturecooling
  3. stirringby stirring for 1 hour at room temperature
  4. filtrationthe precipitated solid was collected by filtration
  5. customThe resulting solid was purified through silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-420fb29c6db5480c93a526d38f2a7e55
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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