Dichloromethane → HCID 24812204, compound

HRID 1945464Notes

Reaction equation

[C:1]12([C:11]3[CH:22]=[CH:21][C:14]([O:15][CH2:16][CH2:17]C(O)=O)=[CH:13][CH:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:23][O:24][C:25](=[O:34])[C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([OH:33])[CH:27]=1.ClCCl.[OH-].[Na+]>C[Si](OP(=O)=O)(C)C>[CH3:23][O:24][C:25]([C:26]1[CH:31]=[CH:30][C:29]2[N:32]=[C:17]([CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([C:1]45[CH2:10][CH:5]6[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]6)[CH2:2]4)[CH2:8]5)=[CH:22][CH:21]=3)[O:33][C:28]=2[CH:27]=1)=[O:34]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of (4-adamantan-1-yl-phenoxymethyl)acetic acid (200.0 mg, 0.70 mmol) and 4-amino-3-hydroxy-benzoic acid methyl ester (164.3 mg, 0.98 mmol) in PPSE (3 mL) was heated at 140° C. for 2 h. At the end of the reaction period, the mixture was taken to dichloromethane and neutralized with 1 N NaOH solution. The organic layer was separated and the aqueous solution extracted with dichloromethane. The combined extracts were dried over anhydrous MgSO4, filtered and the solvent was removed with rotary evaporator under reduced pressure. The residue was purified by flash chromatography (n-Hexane:EtoAc:MeOH=6:3:1) to afford 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid methyl ester as a white solid (184.0 mg, 63.0% yield).

Workup

customAt the end of the reaction period
customThe organic layer was separated
extractionthe aqueous solution extracted with dichloromethane
dry with materialThe combined extracts were dried over anhydrous MgSO4
filtrationfiltered
customthe solvent was removed with rotary evaporator under reduced pressure
customThe residue was purified by flash chromatography (n-Hexane:EtoAc:MeOH=6:3:1)

Sources & evidence

ORD record: ord-69db9c742e1241f0885b8922924b4842
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394799B2

Reaction notes

Loading…