HCID 11299037, compound → HCID 69216070, compound

HRID 2219293Notes

Reaction equation

[N+:1]([C:4]1[C:13]2[O:12][C@@:11]([CH3:19])([CH:14]([O:17][CH3:18])[O:15][CH3:16])[C@H:10]3[O:20][C@H:9]3[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][CH2:29][C:30]2[N:31]=[N:32][N:33]([CH3:35])[N:34]=2)=[CH:24][CH:23]=1>>[N+:1]([C:4]1[C:13]2[O:12][C@@:11]([CH3:19])([CH:14]([O:17][CH3:18])[O:15][CH3:16])[C@@H:10]([OH:20])[C@H:9]([N:28]([C:25]3[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=3)[CH2:29][C:30]3[N:31]=[N:32][N:33]([CH3:35])[N:34]=3)[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 11299037HCID 11299037, compound

HCID 86603167HCID 86603167, compound

Product 1

HCID 69216070HCID 69216070, compoundYield 15%

Procedure

The same procedure as step 3 of example 1 was accomplished, except for using (2R,3S,4S)-8-nitro-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran (751 mg, 2.67 mmol) and N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amine (597 mg, 2.67 mmol). The crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=2:1), to give desired compound (200 mg, yield: 15%).

Workup

customThe crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-a4c614c5a6884faf93bcf2edd83bb864
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414068B2

Reaction notes

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