Citric Acid → HCID 19756390、化合物

HRID 1587834ノート

反応式

HRID 1587834 の反応式
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]

参加物

7

反応物 4

HCID 311Citric AcidHCID 679Dimethyl SulfoxideHCID 14812Phosphorus oxide (P4O10)HCID 19756350HCID 19756350、化合物

生成物 1

HCID 19756390HCID 19756390、化合物収率 46.1%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-55ea0ede57154d598131d0251116df29
出典データセット
uspto-grants-1993_06
特許番号
US05219863

反応ノート

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