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Hydrochloric Acid → (-)-2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

HRID 367349
Notes
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Reaction equation

HRID 367349 reaction equation
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([C@@H: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]([N:29]([CH3:31])[CH3:30])=[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][C@H: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]([N:29]([CH3:31])[CH3:30])=[O:28])=[CH:20][CH:21]=2)[CH2:16]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 70137494(-)-(2R)-2-[(2S)-2-[[2-(2,2-dimethylbenzo[1,2-d]-1,3-dioxan-6-yl)-2-hydroxyethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide

Product 1

HCID 9811600(-)-2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamideYield 81.1%

Reagents, catalysts & solvents

1
HCID 80711,2-DimethoxyethaneSolvent

Procedure

(-)-2-[(2S)-2-[[(2R)-2-(2,2-Dimethylbenzo[1,2-d]-1,3dioxan-6-yl)-hydroxyethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (192 mg) was dissolved in 3.8 ml of 1,2-dimethoxyethane, 4.2 ml of 1 N hydrochloric acid was added to the solution with stirring under ice-cooling, and the mixture was subjected to 2 hours of reaction at room temperature. The reaction solution was neutralized by adding an aqueous saturated sodium bicarbonate solution and then concentrated to dryness under reduced pressure. Tetrahydrofuran and ethanol were added to the resulting residue and insoluble materials were removed by filtration. The resulting filtrate was concentrated under reduced pressure, and the resulting residue was purified by aminopropylated silica gel medium pressure liquid column chromatography (eluent: ethyl acetate/ethanol=5/1) and then recrystallized from methanol to give 142 mg of (-)-2-[(2S)-2-[[(2R)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]-N,N-dimethylacetamide (Compound 6) having a melting point of 175 to 176° C.

Workup

  1. temperaturecooling
  2. customthe mixture was subjected to 2 hours of reaction at room temperature
  3. concentrationconcentrated to dryness under reduced pressure
  4. additionTetrahydrofuran and ethanol were added to the resulting residue and insoluble materials
  5. customwere removed by filtration
  6. concentrationThe resulting filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by aminopropylated silica gel medium pressure liquid column chromatography (eluent: ethyl acetate/ethanol=5/1)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-264b3193e1f84c52be9708cc5df4b144
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06133266

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes