Cesium carbonate → 1-[({[(4R,5R)-3-methyl-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

HRID 889523ノート

反応式

HRID 889523 の反応式
[C:1](=[O:22])([O:18][CH:19](Cl)[CH3:20])[O:2][CH2:3][CH2:4][CH:5]([CH3:17])[CH:6]([O:13][N+:14]([O-:16])=[O:15])[CH:7]([O:9][N+:10]([O-:12])=[O:11])[CH3:8].[CH2:23]([C:27]1[N:28]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[C:49]3[N:53]([C:54]([C:67]4[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=4)([C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)[N:52]=[N:51][N:50]=3)=[CH:39][CH:38]=2)[C:29]([C:33]([OH:35])=[O:34])=[C:30]([Cl:32])[N:31]=1)[CH2:24][CH2:25][CH3:26].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:23]([C:27]1[N:28]([CH2:36][C:37]2[CH:38]=[CH:39][C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[C:49]3[N:53]([C:54]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=4)([C:67]4[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=4)[C:61]4[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=4)[N:52]=[N:51][N:50]=3)=[CH:41][CH:42]=2)[C:29]([C:33]([O:35][CH:19]([O:18][C:1]([O:2][CH2:3][CH2:4][CH:5]([CH3:17])[C@@H:6]([O:13][N+:14]([O-:16])=[O:15])[C@H:7]([O:9][N+:10]([O-:12])=[O:11])[CH3:8])=[O:22])[CH3:20])=[O:34])=[C:30]([Cl:32])[N:31]=1)[CH2:24][CH2:25][CH3:26]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 467832052-Butyl-4-chloro-1-({2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl}methyl)-1H-imidazole-5-carboxylic acid2 回HCID 866470213-Methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

生成物 1

HCID 866470201-[({[(4R,5R)-3-methyl-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(4R,5R))-3-methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate (1.01 g, 3.26 mmol) was added to a stirred solution of 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid (Intermediate 3, 3.32 g, 4.88 mmol) and Cs2CO3 (2.40 g, 7.33 mmol) in DMF (18 mL). The solution was stirred at room temperature overnight. The mixture was diluted with a solution of NaH2PO4 5% (40 mL) and extracted with EtOAc (3×25 mL). The organic layer was washed with water (4×20 mL) and brine. The residue was purified by flash chromatography (Biotage SP1, SNAP 100 g column, TLC method: n-Hexane/EtOAc 7:3, RE 0.45) affording the title compound that was used in the next step without any further characterization.

後処理

  1. extractionextracted with EtOAc (3×25 mL)
  2. washThe organic layer was washed with water (4×20 mL) and brine
  3. customThe residue was purified by flash chromatography (Biotage SP1, SNAP 100 g column, TLC method

出典と根拠

ORDレコード
ord-0cba5b11570d433eaf93c2345defd5ce
出典データセット
uspto-grants-2012_08
特許番号
US08252825B2

反応ノート

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