HCID 11299037, compound → HCID 10099166, compound

HRID 2219290Notes

Reaction equation

[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][C@@:13]([CH3:20])([CH:15]([O:18][CH3:19])[O:16][CH3:17])[C@H:12]3[O:21][C@H:11]3[C:10]=2[CH:22]=1)(=[O:4])=[O:3].[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][CH2:31][C:32]2[N:33]=[N:34][N:35]([CH3:37])[N:36]=2)=[CH:26][CH:25]=1>>[CH3:1][S:2]([O:5][C:6]1[CH:7]=[CH:8][C:9]2[O:14][C@@:13]([CH3:20])([CH:15]([O:16][CH3:17])[O:18][CH3:19])[C@@H:12]([OH:21])[C@H:11]([N:30]([C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=3)[CH2:31][C:32]3[N:33]=[N:34][N:35]([CH3:37])[N:36]=3)[C:10]=2[CH:22]=1)(=[O:3])=[O:4]

Participants

Reactant 2

HCID 11299037HCID 11299037, compound

HCID 86603165HCID 86603165, compound

Product 1

HCID 10099166HCID 10099166, compoundYield 27%

Procedure

The same procedure as step 3 of example 1 was accomplished, except for using (2R,3S,4S)-6-methane sulfonyloxy-2-methyl-2-dimethoxymethyl-3,4-epoxy-3,4-dihydro-2H-1-benzopyran (231 mg, 0.70 mmol) and N-(4-chlorophenyl)-N-(2-methyl-2H-tetrazol-5-ylmethyl)amine (187 mg, 0. 84 mmol). The crude product was purified by silica gel column chromatography (developing solvent-n-hexane:ethyl acetate=1:1), to give desired compound (104 mg, yield: 27%).

Workup

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

Sources & evidence

ORD record: ord-b026f471c52248a2bd1bc33763039524
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414068B2

Reaction notes

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