Dimethyl L-aspartate hydrochloride → Dimethyl 2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)succinate

HRID 45651Notes

Reaction equation

HRID 45651 reaction equation
Cl.[NH2:2][CH:3]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:4]([O:6][CH3:7])=[O:5].[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([Cl:24])[CH:23]=1)[CH2:20][N:19]([CH3:25])[CH2:18][CH:17]2[C:26]1[CH:27]=[C:28]([S:32](Cl)(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1>N1C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([Cl:24])[CH:23]=1)[CH2:20][N:19]([CH3:25])[CH2:18][CH:17]2[C:26]1[CH:27]=[C:28]([S:32]([NH:2][CH:3]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[C:4]([O:6][CH3:7])=[O:5])(=[O:34])=[O:33])[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 3084560Dimethyl L-aspartate hydrochlorideHCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 70906016Dimethyl 2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)succinateYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of dimethyl 2-aminosuccinate hydrochloride (107 mg, 0.54 mmol, 1.00 equiv) in pyridine (5 mL). This was followed by the addition of 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (300 mg, 0.69 mmol, 1.27 equiv, 90%) in several batches. The resulting solution was stirred overnight at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane:methanol (50:1). This resulted in 200 mg (72%) of the title compound as a colorless oil

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-8561e86cb9c247b5a674db677cdca1ae
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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