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 889523노트

반응식

HRID 889523 반응식
[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]

참가 물질

5

반응물 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 acid2회HCID 866470213-Methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

생성물 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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-0cba5b11570d433eaf93c2345defd5ce
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252825B2

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