Citric Acid → HCID 19756390, Verbindung

HRID 1587834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587834
CS(C)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:19]([C:21]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[N:46]=[N:47][N:48]([C:50]([C:63]4[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=4)([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:49]=3)=[CH:35][CH:34]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:69][CH2:70][CH2:71][OH:72])[N:27]=2)[N:22]=1)[CH3:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.C(N(CC)CC)C>[CH2:19]([C:21]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[C:45]3[N:46]=[N:47][N:48]([C:50]([C:63]4[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=4)([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[N:49]=3)=[CH:37][CH:38]=2)[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:69][CH2:70][CH:71]=[O:72])[N:27]=2)[N:22]=1)[CH3:20]

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 14812Phosphorus oxide (P4O10)HCID 19756350HCID 19756350, Verbindung

Produkt 1

HCID 19756390HCID 19756390, VerbindungAusbeute 46,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

DMSO (2.0 ml) and phosphorus pentoxide (4.0 g) were added to a solution of 2-ethyl-6-(2-hydroxyethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (1.0 g) in dichloromethane (20 ml) at 0° C. The mixture was stirred at ambient temperature for 1 hour and then cooled again to 0° C. Triethylamine (0.69 ml) was added and stirring was continued for 30 minutes. 1M citric acid solution (20 ml) was added and the organic phase was separated and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:1 v/v), to give 2-ethyl-6-(formylmethoxy)-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-1,5-naphthyridine (B) (0.46 g), m.p. 168°-169° C. (after trituration with ether; NMR (d6 -DMSO): 1.25(t, 3H), 2.9(q, 2H), 5.0(s, 2H), 5.35(s, 2H), 6.8-6.95(m, 6H), 7.1-7.85(m, 19H), 8.25(d, 1H), 9.7(s, 1H).

Aufarbeitung

  1. temperaturecooled again to 0° C
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. customthe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:1 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-55ea0ede57154d598131d0251116df29
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05219863

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