(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid → HCID 12085095, compound

HRID 2083997Notes

Reaction equation

HRID 2083997 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@H:3]([C:11]([OH:13])=[O:12])[NH:2]1.[N+:14]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]>[OH-].[Na+].O1CCCC1>[N+:14]([C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([N:2]3[C@@H:3]([C:11]([OH:13])=[O:12])[CH2:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH2:1]3)(=[O:31])=[O:30])=[CH:25][CH:24]=2)=[CH:21][CH:22]=1)([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 712398(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acidHCID 27601854'-Nitrobiphenyl-4-sulfonyl chloride

Product 1

HCID 12085095HCID 12085095, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

44.2 g (250 mmol) of 1,2,3,4-tetrahydroisoquinoline-3-(R)-carboxylic acid were dissolved in 500 ml of 1N aqueous sodium hydroxide solution and, while stirring, 150 g (300 mmol) of 4′-nitrobiphenyl-4-sulfonyl chloride dissolved in 500 ml of tetrahydrofuran were added. During this, the reaction temperature was kept below 25° C., and the pH of the solution was adjusted to pH 10 by adding 1N NaOH. The reaction mixture was stirred at room temperature for 12 hours (h).

Workup

  1. additionwere added
  2. customwas kept below 25° C.
  3. stirringThe reaction mixture was stirred at room temperature for 12 hours (h)

Sources & evidence

ORD record
ord-6b58e466ea234ca6b1c7588f3fce1897
Source dataset
uspto-grants-2004_04
Patent number
US06716853B2

Reaction notes

Loading…