Hydrochloric Acid → HCID 15453436, compound

HRID 1003272Notes

Reaction equation

HRID 1003272 reaction equation
[OH:1][CH:2]([C:22]1[CH:27]=[CH:26][C:25]([O:28]C2CCCCO2)=[CH:24][CH:23]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[OH:1][CH:2]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH2:3][NH:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:11]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 21967811HCID 21967811, compound

Product 1

HCID 15453436HCID 15453436, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-[(2S)-2-[[(2RS)-2-hydroxy-2-[4-((2RS)-2-tetrahydropyranyloxy)phenyl]ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (780 mg) was dissolved in ethanol (20 ml), and 1N hydrochloric acid (34 ml) was added to the solution under ice-cooling with stirring. After reaction for an hour, the reaction mixture was neutralized with a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: ethyl acetate) gave ethyl 2-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]acetate (238 mg) as an amorphous.

Workup

  1. temperaturecooling
  2. customAfter reaction for an hour
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-eec830a3a421414c82dd24dd91fa9c6c
Source dataset
uspto-grants-2000_04
Patent number
US06046192

Reaction notes

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