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 889523Notes

Reaction equation

HRID 889523 reaction equation
[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]

Participants

5

Reactant 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×HCID 866470213-Methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate

Product 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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-0cba5b11570d433eaf93c2345defd5ce
Source dataset
uspto-grants-2012_08
Patent number
US08252825B2

Reaction notes

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