Hydrochloric Acid → HCID 54304925, compound

HRID 367347Notes

Reaction equation

HRID 367347 reaction equation
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]([OH:32])[CH2:13][NH:14][C@H:15]3[CH2:24][CH2:23][C:22]4[C:17](=[CH:18][C:19]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20][CH:21]=4)[CH2:16]3)=[CH:11][C:5]=2[CH2:4][O:3]1.Cl.C(=O)(O)[O-].[Na+]>COCCOC>[OH:32][CH:12]([C:10]1[CH:9]=[CH:8][C:6]([OH:7])=[C:5]([CH2:4][OH:3])[CH:11]=1)[CH2:13][NH:14][C@H:15]1[CH2:24][CH2:23][C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:20][CH:21]=2)[CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 70125814HCID 70125814, compound

Product 1

HCID 54304925HCID 54304925, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-[(2S)-2-[[(2RS)-2-(2,2-dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-2-hydroxyethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (11.5 g) was suspended in 75 ml of 1,2-dimethoxyethane, 252 ml of 1 N hydrochloric acid was added dropwise to the suspension while keeping the temperature at 20° C. or lower, and the resulting mixture was subjected to 30 minutes of reaction at room temperature. Then, 23.3 g of sodium bicarbonate was added with stirring at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with an aqueous saturated sodium bicarbonate solution and brine and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was evaporated under reduced pressure and the resulting residue was purified by silica gel medium pressure liquid column chromatography (eluent: ethyl acetate/ethanol=5/1) to give 7.2 g of amorphous ethyl 2-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate.

Workup

  1. customat 20° C.
  2. customlower, and the resulting mixture was subjected to 30 minutes of reaction at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with an aqueous saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThereafter, the solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel medium pressure liquid column chromatography (eluent: ethyl acetate/ethanol=5/1)

Sources & evidence

ORD record
ord-55cbbdbb703049688c715f4c2833338e
Source dataset
uspto-grants-2000_10
Patent number
US06133266

Reaction notes

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