Hydrochloric Acid → HCID 178435493, compound

HRID 1614598Notes

Reaction equation

HRID 1614598 reaction equation
[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[C@@H:30]([CH3:31])[C@H:29]([CH2:32][CH2:33][C:34]([O:36]C)=[O:35])[C:15]([C:16]5[CH2:27][C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:28])=[CH:20]2)=[N:14]4)=[C:9]([CH3:38])[C:8]=3[CH:39]=[CH2:40])[C:4]=1[CH3:41].Cl.CO.ClCCl>O1CCCC1>[CH3:1][CH2:2][C:3]1[C:21]2=[N:22][C:5](=[CH:6][C:7]3[NH:11][C:10]([CH:12]=[C:13]4[C@@H:30]([CH3:31])[C@H:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])[C:15]([C:16]5[CH2:27][C:25](=[O:26])[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:28])=[CH:20]2)=[N:14]4)=[C:9]([CH3:38])[C:8]=3[CH:39]=[CH2:40])[C:4]=1[CH3:41]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226129Dichloromethane methanolHCID 178435492HCID 178435492, compound

Product 1

HCID 178435493HCID 178435493, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl pyropheophorbide-a (2, 250 mg) was dissolved in distilled tetrahydrofuran (50 ml) and 4N HCl (125 ml) was added in one lot. The reaction mixture was stirred under nitrogen atmosphere at room temperature for 4 hours. The reaction was monitored by analytical tlc (silica plates), using 10% methanol/dichloromethane as a mobile phase. The reaction mixture was then poured in ice water, extracted with dichloromethane. The dichloromethane layer was washed several times with water (3×200 ml). The organic layer was separated and dried over anhydrous sodium sulfate. Evaporation of the solvent gave a residue, which was crystallized from dichloromethane/hexane. Yield, 225 mg. The purity of the compound was ascertained by tlc and the structure was confirmed by NMR spectroscopy. The NMR data were similar as described for 2 except the resonances for the --OCH3 protons of the propionic ester (--CH2CH2CO2CH3) were missing.

Workup

  1. extractionextracted with dichloromethane
  2. washThe dichloromethane layer was washed several times with water (3×200 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent
  6. customgave a residue, which
  7. customwas crystallized from dichloromethane/hexane
  8. customYield

Sources & evidence

ORD record
ord-f507a363d5874b6488c6ff351bc4f800
Source dataset
uspto-grants-1993_03
Patent number
US05198460

Reaction notes

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