Hydrochloric Acid → HCID 178435493, compound

HRID 1823696Notes

Reaction equation

HRID 1823696 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 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-3c7ed895a3d14617ac58eab0e1c234db
Source dataset
uspto-grants-2006_05
Patent number
USRE039094E1

Reaction notes

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