Hydrochloric Acid → HCID 70378705, compound

HRID 1380136Notes

Reaction equation

HRID 1380136 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:20]([OH:34])[CH2:21][NH:22][C@@H:23]([CH3:33])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2)C1C=CC=CC=1.[ClH:35]>[Pd].O1CCCC1>[ClH:35].[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:20]([OH:34])[CH2:21][NH:22][C@@H:23]([CH3:33])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[CH:14]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14233147HCID 14233147, compound

Product 1

HCID 70378705HCID 70378705, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 916 mg of 8-benzyloxy-5-{(1S)-1-hydroxy-2-[N-((1S)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril, 100 mg of 10% palladium-charcoal, 2 ml of 1N hydrochloric acid and 20 ml of tetrahydrofuran is shaken at room temperature at an atmospheric pressure under a hydrogen atmosphere for 2 hours. Insoluble materials are collected by filtration and washed with an aqueous 10% ethanol solution. The filtrate and washings are combined, and the combined solution is concentrated under reduced pressure to remove solvent. The residue is crystallized with a mixture of methanol and ether, and crystalline precipitates are collected by filtration. 623 mg of 8-hydroxy-5-{(1S)-1-hydroxy-2-[N-((1S)-2-(p-methoxyphenyl)-1-methylethyl)amino]ethyl}carbostyril hydrochloride are obtained as colorless crystals. Yield: 77%

Workup

  1. filtrationInsoluble materials are collected by filtration
  2. washwashed with an aqueous 10% ethanol solution
  3. concentrationthe combined solution is concentrated under reduced pressure
  4. customto remove solvent
  5. customThe residue is crystallized with a mixture of methanol and ether
  6. customcrystalline precipitates
  7. filtrationare collected by filtration

Sources & evidence

ORD record
ord-ec2b59c505354f7f910d4a5d5da68e92
Source dataset
uspto-grants-1986_04
Patent number
US04579854

Reaction notes

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