Hydrochloric Acid → HCID 444698, compound

HRID 651251Notes

Reaction equation

HRID 651251 reaction equation
[OH-].[Na+].[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C@H:5]([C:13]([OH:15])=[O:14])[NH:4]1.[C:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>O.O1CCCC1>[C:16]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:19]([S:22]([N:4]2[C@@H:5]([C:13]([OH:15])=[O:14])[CH2:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:3]2)(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 712398(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid

Product 1

HCID 444698HCID 444698, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (13.6 g) is dissolved in water (300 ml), and therein is suspended (3R)-1,2,3,4-tetrahydro-3-isoquinolinecarboxlic acid (30.0 g) and thereto is added tetrahydrofuran (120 ml). To the resulting solution is added 4-biphenylylsulfonyl chloride (42.9 g), and the mixture is stirred at room temperature for one hour. The reaction mixture is acidified with 10% hydrochloric acid under ice cooling, and is diluted with water, and then extracted twice with ethyl acetate. The extract is washed with water and an aqueous saturated saline solution, dried over sodium sulfate and then treated with active carbon. Undissolved materials are filtered off from the extract, and the solvent is distilled off under reduced pressure. The residue is recrystallized from ethyl acetate-hexane to give (3R)-N-(4-biphenylylsulfonyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (36.5 g) as colorless crystals.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe extract is washed with water
  3. dry with materialan aqueous saturated saline solution, dried over sodium sulfate
  4. additiontreated with active carbon
  5. filtrationUndissolved materials are filtered off from the extract
  6. distillationthe solvent is distilled off under reduced pressure
  7. customThe residue is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e7727373956e459b83ae43876dbec5fe
Source dataset
uspto-grants-2001_08
Patent number
US06277992B1

Reaction notes

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