Benzoyl chloride → HCID 178427464, compound

HRID 129870Notes

Reaction equation

HRID 129870 reaction equation
[C:1]1([N:7]2[CH2:13][CH2:12][C:11]([C:14]([C:38](OC(C)(C)C)=[O:39])([C:16](=[O:37])[C@H:17]([CH2:30][CH2:31][CH2:32][NH:33][C:34](=[NH:36])[NH2:35])[N:18]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH3:19])[NH2:15])=[CH:10][CH:9]([CH2:45][C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[C:8]2=[O:56])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1.C(N(CC)CC)C.C(Cl)(=O)[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>>[C:1]1([N:7]2[CH2:13][CH2:12][C:11]([C:14]([C:38](=[O:39])[C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)([C:16](=[O:37])[C@H:17]([CH2:30][CH2:31][CH2:32][NH:33][C:34](=[NH:36])[NH2:35])[N:18]([S:20]([C:23]3[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=3)(=[O:21])=[O:22])[CH3:19])[NH2:15])=[CH:10][CH:9]([CH2:45][C:46]([O:48][CH2:49][C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)=[O:47])[C:8]2=[O:56])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 204431481,4-Dioxane hydrochlorideHCID 178427465HCID 178427465, compound

Product 1

HCID 178427464HCID 178427464, compoundYield 61%

Procedure

Compound (16) (69 mg, 0.087 mmol) from above was treated with anhydrous HCl/dioxane (5 mL) at room temperature for 4 h. The reaction mixture was then evaporated at reduced pressure and then re-evaporated at reduced pressure 2× from toluene to remove any excess HCl. The residue was dissolved in N,N-dimethylformamide (5 mL) and treated with triethylamine (24 μL, 0.174 mmol) and benzoyl chloride (20 μL, 0.174 mmol) at room temperature for 18 h. The reaction mixture was then evaporated under high vacuum and the residue was purified by flash chromatography (silica gel, 2.5×20 cm, 2% methanol in chloroform) to yield the title compound (17) (42 mg, 61%) as an inseparable mixture of diastereoisomers. Compound (17): TLC Rf 0.58 (silica gel, 9:1 chloroform: methanol).

Workup

  1. customThe reaction mixture was then evaporated at reduced pressure
  2. customre-evaporated at reduced pressure 2× from toluene
  3. customto remove any excess HCl
  4. dissolutionThe residue was dissolved in N,N-dimethylformamide (5 mL)
  5. customThe reaction mixture was then evaporated under high vacuum
  6. customthe residue was purified by flash chromatography (silica gel, 2.5×20 cm, 2% methanol in chloroform)

Sources & evidence

ORD record
ord-6215af389a45483b83a2ddaed6ef029a
Source dataset
uspto-grants-1995_11
Patent number
US05470849

Reaction notes

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