Triethylamine → HCID 15487111, compound

HRID 1858925Notes

Reaction equation

HRID 1858925 reaction equation
[NH2:1][C@@H:2]([CH2:4][OH:5])[CH3:3].C(N(CC)CC)C.Cl[S:14]([C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[C:19]([CH3:27])=[CH:20][N:21]=[CH:22]2)(=[O:16])=[O:15]>C(Cl)Cl.O>[CH3:27][C:19]1[C:18]2[C:23](=[CH:24][CH:25]=[CH:26][C:17]=2[S:14]([NH:1][C@H:2]([CH3:3])[CH2:4][OH:5])(=[O:16])=[O:15])[CH:22]=[N:21][CH:20]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 154871104-Methylisoquinoline-5-sulfonyl chloride

Product 1

HCID 15487111HCID 15487111, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 g of D-alaninol in 50 ml of methylene chloride was added 2.02 g of triethylamine, and after addition of 3.22 g of 5-chlorosulfonyl-4-methylisoquinoline under ice-cooling, the mixture was stirred for 2 hours. This reaction mixture was diluted with water and extracted with methylene chloride and the extract was dried and concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) to provide 3.0 g of (R)-2-[(4-methyl-5-isoquinolinyl)sulfonyl amino]-1-propanol (white crystals).

Workup

  1. temperaturecooling
  2. extractionextracted with methylene chloride
  3. customthe extract was dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-378d42c05af5488793defb072039c529
Source dataset
uspto-grants-2000_11
Patent number
US06153608

Reaction notes

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