Triethylamine → HCID 18698336, compound

HRID 2289808Notes

Reaction equation

HRID 2289808 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][N:8]([S:17]([C:20]1[CH:29]=[C:28]2[C:23]([C:24]([Cl:31])=[CH:25][N:26]=[C:27]2[Cl:30])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])CCC.[C:33](OC(=O)CNCC1C=CC=CC=1C)([CH3:36])([CH3:35])[CH3:34].CCN(CC)CC>C(Cl)Cl>[C:33]([O:5][C:6](=[O:32])[CH2:7][N:8]([S:17]([C:20]1[CH:29]=[C:28]2[C:23]([C:24]([Cl:31])=[CH:25][N:26]=[C:27]2[Cl:30])=[CH:22][CH:21]=1)(=[O:18])=[O:19])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18698203HCID 18698203, compoundHCID 18698420HCID 18698420, compound

Product 1

HCID 18698336HCID 18698336, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[(1,4-Dichloro-7-isoquinolinyl)sulphonyl]-N-(2-methylbenzyl)glycine 1-butyl ester ##STR121## 1,4-Dichloro-7-isoquinolinesulphonyl chloride (400 mg, 1.35 mmol) was added to a stirred solution of N-(2-methylbenzyl)glycine t-butyl ester (380 mg, 1.61 mmol) in CH2Cl2 (20 mL) containing NEt3 (0.28 mL, 2.5 mmol) under N2 and the mixture was stirred at room temperature for 18 h. The mixture was diluted with CH2Cl2 and washed with dilute HCl (2 M), saturated aqueous NaHCO3, brine, dried (MgSO4) then and evaporated in vacuo. The residue was purified by column chromatography upon silica gel using pentane-EtOAc (100:0 to 90:10) as eluant to give N-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]-N-(2-methylbenzyl)glycine t-butyl ester (480 mg, 0.97 mmol) as a white solid.

Workup

  1. washwashed with dilute HCl (2 M), saturated aqueous NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography upon silica gel

Sources & evidence

ORD record
ord-12be04096b864e018559aa4844e178d4
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

Loading…