17499-98-8 → HCID 9809054, compound

HRID 497554Notes

Reaction equation

HRID 497554 reaction equation
[CH3:1][CH2:2][C@H:3]1[C:7]2=[CH:8][C:9]3[N-:13][C:12]4[C:14]([C@@H:57]([C:60]([O:62][CH3:63])=[O:61])[C:58](=[O:59])[C:11]=4[C:10]=3[CH3:64])=[C:15]3[N:19]=[C:18]([CH:20]=[C:21]4[N-:26][C:24](=[CH:25][C:5](=[N:6]2)[C@@H:4]1[CH3:65])[C:23]([C:27]([CH3:29])=[O:28])=[C:22]4[CH3:30])[C@@H:17]([CH3:31])[C@@H:16]3[CH2:32][CH2:33][C:34]([O:36]C/C=C(/CCC[C@@H](CCC[C@@H](CCCC(C)C)C)C)\C)=[O:35].[Mg+2]>FC(F)(F)C(O)=O.O>[CH3:1][CH2:2][C@H:3]1[C:7]2=[CH:8][C:9]3[NH:13][C:12]4[C:14]([C@@H:57]([C:60]([O:62][CH3:63])=[O:61])[C:58](=[O:59])[C:11]=4[C:10]=3[CH3:64])=[C:15]3[N:19]=[C:18]([CH:20]=[C:21]4[NH:26][C:24](=[CH:25][C:5](=[N:6]2)[C@@H:4]1[CH3:65])[C:23]([C:27]([CH3:29])=[O:28])=[C:22]4[CH3:30])[C@@H:17]([CH3:31])[C@@H:16]3[CH2:32][CH2:33][C:34]([OH:36])=[O:35]

Participants

4

Reactant 1

HCID 1195394717499-98-8

Product 1

HCID 9809054HCID 9809054, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of bacteriochlorophyll a (15) (45 mg, 0.05 mmol, a product of Sigma-Aldrich Corp.) in a mixture of trifluoroacetic acid (1.2 mL) and water (0.3 mL) was kept at room temperature for 3 hours, concentrated in vacuum (˜20 mmHg) at room temperature, diluted with water and extracted with dichloromethane. The extracts were washed with water, dried, concentrated, and purified on Silica gel with a mixture of 5% MeOH—CHCl3 to give 31 mg (98%) of bacteriopheophorbide a (14).

Workup

  1. concentrationconcentrated in vacuum (˜20 mmHg) at room temperature
  2. additiondiluted with water
  3. extractionextracted with dichloromethane
  4. washThe extracts were washed with water
  5. customdried
  6. concentrationconcentrated
  7. custompurified on Silica gel with a mixture of 5% MeOH—CHCl3

Sources & evidence

ORD record
ord-a8a608b8ade645239539acd80f3624fa
Source dataset
uspto-grants-2005_09
Patent number
US06949581B2

Reaction notes

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