Hydrochloric Acid → 2-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid

HRID 1945471Notes

Reaction equation

HRID 1945471 reaction equation
C[O:2][C:3]([C:5]1[CH:31]=[CH:30][C:8]2[N:9]=[C:10]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]45[CH2:29][CH:24]6[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]6)[CH2:21]4)[CH2:27]5)=[CH:16][CH:15]=3)[O:11][C:7]=2[CH:6]=1)=[O:4].[Br-].[Al+3].[Br-].[Br-].O.Cl>CSC.ClCCl>[C:20]12([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:10]4[O:11][C:7]5[CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:31]=[CH:30][C:8]=5[N:9]=4)=[CH:15][CH:16]=3)[CH2:27][CH:26]3[CH2:28][CH:22]([CH2:23][CH:24]([CH2:25]3)[CH2:29]1)[CH2:21]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 166749BromhydrolHCID 24812204HCID 24812204, compound

Product 1

HCID 249665352-(4-Adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acidYield 77.8%

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid methyl ester (110 mg, 0.26 mmol) in dimethyl sulfide (10 ml) and dichloromethane (10 ml) was added aluminum bromide (1.13 g, 4.22 mmol). The reaction mixture was stirred at room temperature for 2.5 h, after which water and 10% HCl were added. After stirring at room temperature for 1 h, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by silica gel flash column chromatography (CH2Cl2:MeOH=4:1) to give 2-(4-adamantan-1-yl-phenoxymethyl)-benzoxazole-6-carboxylic acid as a white solid (81.6 mg, 76.8% yield).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. customthe mixture was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel flash column chromatography (CH2Cl2:MeOH=4:1)

Sources & evidence

ORD record
ord-d7057b2e7cab4f058349487f59f2b7e1
Source dataset
uspto-grants-2013_03
Patent number
US08394799B2

Reaction notes

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