Hydrochloric Acid → HCID 53920425, compound

HRID 369371Notes

Reaction equation

HRID 369371 reaction equation
CC1(C)[O:7][C:6]2[CH:8]=[CH:9][C:10]([CH:12]([OH:35])[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][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:20][CH:21]=4)[CH2:16]3)=[CH:11][C:5]=2[CH2:4][O:3]1.Cl>O1CCCC1>[OH:35][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][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:20][CH:21]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70124715HCID 70124715, compound

Product 1

HCID 53920425HCID 53920425, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-[(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]valerate (207 mg) was dissolved in tetrahydrofuran (2 ml), and 1 N hydrochloric acid (2.0 ml) was added to the solution at room temperature. After reaction for an hour, the reaction mixture was concentrated in vacuo. A saturated aqueous sodium bicarbonate solution was added to the residue, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: chloroform/methanol=10/1) gave ethyl 5-[(2S)-2-[[(2RS)-2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)ethyl]amino]-1,2,3,4-tetrahydronaphthalen-7-yloxy]valerate (Compound 1) (125 mg) as an amorphous.

Workup

  1. customAfter reaction for an hour
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionA saturated aqueous sodium bicarbonate solution was added to the residue
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customPurification of the residue by medium pressure liquid column chromatography on aminopropyl silica gel (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-972a7d5b05b24183882355b5eb32f284
Source dataset
uspto-grants-2000_10
Patent number
US06136852

Reaction notes

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