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Water → (2S-trans)-18-Carboxy-20-(carboxymethyl)-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-8-vinyl-21H,23H-porphine-2-propionic acid; (17S,18S)-18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid

HRID 359757
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 359757
[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[CH:34]([CH3:35])[CH:33]([CH2:36][CH2:37][C:38]([O:40]C)=[O:39])[C:15]([C:16]5[CH:27]([C:28]([O:30]C)=[O:29])C(=O)[C:24]6[C:17]=5[NH:18][C:19]([C:23]=6[CH3:32])=[CH:20]2)=[N:14]4)=[C:9]([CH3:42])[C:8]=3[CH:43]=[CH2:44])[C:4]=1[CH3:45].[CH3:46][O-:47].[Na+].[Na].[OH2:50]>O1CCCC1.CO>[CH3:1][CH2:2][C:3]1[C:21]2[N:22]=[C:5]([CH:6]=[C:7]3[C:8]([CH:43]=[CH2:44])=[C:9]([CH3:42])[C:10](=[CH:12][C:13]4[C@@H:34]([CH3:35])[C@H:33]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[C:15](=[C:16]([CH2:27][C:28]([OH:30])=[O:29])[C:17]5[NH:18][C:19]([CH:20]=2)=[C:23]([CH3:32])[C:24]=5[C:46]([OH:50])=[O:47])[N:14]=4)[NH:11]3)[C:4]=1[CH3:45]
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Komponenten

7

Edukt 4

HCID 962WaterHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 178435494HCID 178435494, Verbindung

Produkt 1

HCID 138978174(2S-trans)-18-Carboxy-20-(carboxymethyl)-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-8-vinyl-21H,23H-porphine-2-propionic acid; (17S,18S)-18-(2-Carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid
Ausbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The procedure of Smith and Bushell (M.J. Bushell, Ph.D. Thesis, Univ. of Liverpool, U.K., 1978) was used. The starting material, 1 gm of methyl pheophorbide-a, was dissolved in dry tetrahydrofuran (THF). To this was added sodium methoxide prepared by dissolving 200 mg sodium in 40 ml methanol, and the reaction was allowed to stir at room temperature for 1 hr. The mixture was poured into water and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The residue was dissolved in chloroform and treated with dichloromethane and ether, and the solid obtained was chromatographed on Alumina (Grade III) and eluted with toluene/dichloromethane 1/1. The major band, chlorin-e6 tetramethyl ester was recrystallized from dichloromethane/methanol to obtain 700 mg or 67% yield of the compound of formula ##STR6## By re-utilizing the remaining starting material, an overall yield of 88.7% was obtained, and the structure was confirmed by NMR spectroscopy.

Aufarbeitung

  1. customprepared
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. dissolutionThe residue was dissolved in chloroform
  7. additiontreated with dichloromethane and ether
  8. customthe solid obtained
  9. customwas chromatographed on Alumina (Grade III)
  10. washeluted with toluene/dichloromethane 1/1
  11. customThe major band, chlorin-e6 tetramethyl ester was recrystallized from dichloromethane/methanol

Quellen und Nachweise

ORD-Eintrag
ord-48132f501fc44cdf97719d38a57a5c40
Quelldatensatz
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05002962

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