Thionyl Chloride → HCID 178456588, compound

HRID 892098Notes

Reaction equation

HRID 892098 reaction equation
[CH:1]1([C:6]2[NH:14][C:13]3[C:12]([NH:15][C@@H:16]([CH2:19][C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)[CH2:17]O)=[N:11][C:10](=[O:26])[N:9]([CH2:27][CH2:28][CH3:29])[C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O>>[CH:1]1([C:6]2[NH:14][C:13]3[C:12]4=[N:15][C@@H:16]([CH2:19][C:20]5[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=5)[CH2:17][N:11]4[C:10](=[O:26])[N:9]([CH2:27][CH2:28][CH3:29])[C:8]=3[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 69662557HCID 69662557, compound

Product 1

HCID 178456588HCID 178456588, compoundYield 56.1%

Conditions

Temperature
60 °C

Procedure

To Compound 1a (578 mg, 1.46 mmol) was added thionyl chloride (5.0 mL, 68.5 mmol, 47 equivalents) and the mixture was stirred at 60° C. for 2 hours. Excess thionyl chloride was evaporated, to the resulting residue were added chloroform (10 mL) and saturated aqueous sodium hydrogen carbonate (10 mL), and the mixture was stirred at room temperature for 12 hours. The reaction mixture was extracted with chloroform, the organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=98:2), and chloroform and methanol were added to the residue. The deposited crystals were collected by filtration to obtain the title compound (310 mg, 56%) as a white solid.

Workup

  1. customExcess thionyl chloride was evaporated, to the resulting residue
  2. additionwere added chloroform (10 mL) and saturated aqueous sodium hydrogen carbonate (10 mL)
  3. stirringthe mixture was stirred at room temperature for 12 hours
  4. extractionThe reaction mixture was extracted with chloroform
  5. washthe organic layer was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=98:2), and chloroform and methanol
  9. additionwere added to the residue
  10. filtrationThe deposited crystals were collected by filtration

Sources & evidence

ORD record
ord-62f587215d0a4645bef53355c6e36d17
Source dataset
uspto-grants-2006_02
Patent number
US07005430B2

Reaction notes

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