Ammonia → HCID 69058857, compound

HRID 2221362Notes

Reaction equation

[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8](=[O:23])[CH2:9][C:10]2[CH:19]=[CH:18][C:17]3[O:16][C:15]([CH3:21])([CH3:20])[CH:14]4[O:22][CH:13]4[C:12]=3[CH:11]=2)=[CH:4][CH:3]=1.[NH3:26]>C(O)C>[NH2:26][CH:13]1[C:12]2[C:17](=[CH:18][CH:19]=[C:10]([CH2:9][C:8]([NH:7][CH2:6][C:5]3[CH:24]=[CH:25][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:23])[CH:11]=2)[O:16][C:15]([CH3:21])([CH3:20])[CH:14]1[OH:22]

Participants

Conditions

Temperature: 50 °C

Procedure

The N-(4-chlorobenzyl)-2-(2,2-dimethyl-1a,7b-dihydro-2H-oxireno[c]chromen-6-yl) acetamide obtained above was immediately poured into a mixture of so much ethanol and 25%-strength aqueous ammonia solution (6:5 v/v) that a 0.2 M solution of the compound was obtained, and the resulting solution was stirred for 16 hours at 50° C. Then the solution was allowed to cool to room temperature, and the solvent was largely evaporated at reduced pressure. The remaining residue was chromatographed on silica gel (mobile phase: gradient dichloromethane/methanol/25%-strength aqueous ammonia solution 97.5:2:0.5 to 90:9.5:0.5 v/v/v). Drying of the product fractions yielded 7.3 g 2-(4-amino-3-hydroxy-2,2-dimethyl-3,4-dihydro-2H-chromen-6-yl)-N-4-chlorobenzyl acetamide, which was used without further purification for the subsequent reaction. The other regioisomer, 2-[3-amino-4-hydroxy-2,2-dimethylchromen-6-yl]-N-4-chlorobenzyl acetamide, was not observed.

Workup

customwas obtained
temperatureto cool to room temperature
customthe solvent was largely evaporated at reduced pressure
customThe remaining residue was chromatographed on silica gel (mobile phase: gradient dichloromethane/methanol/25%-strength aqueous ammonia solution 97.5:2:0.5 to 90:9.5:0.5 v/v/v)
customDrying of the product fractions

Sources & evidence

ORD record: ord-a83dc05f50734b1e94fa4f34f2707267
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368582B2

Reaction notes

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