Triethylamine → HCID 178496913, compound

HRID 2419031Notes

Reaction equation

HRID 2419031 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH:4]([C:12]([O:14][CH3:15])=[O:13])[NH:3]1.C(N(CC)CC)C.N#N.Cl.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[CH:34]=[C:33]([S:40]([NH:43][C@H:44]([C:52](Cl)=[O:53])[CH2:45][CH2:46][CH2:47][NH:48][C:49](=[NH:51])[NH2:50])(=[O:42])=[O:41])[CH:32]=[CH:31]2>C(Cl)(Cl)Cl>[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][C:37]=1[O:38][CH3:39])[CH:34]=[C:33]([S:40]([NH:43][C@H:44]([C:52]([N:3]1[CH:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:2]1)=[O:53])[CH2:45][CH2:46][CH2:47][NH:48][C:49](=[NH:50])[NH2:51])(=[O:41])=[O:42])[CH:32]=[CH:31]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122480673-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, methyl ester, hydrochloride (1:1)HCID 178486632HCID 178486632, compound

Product 1

HCID 178496913HCID 178496913, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1.8 g of methyl 1,2,3,4-tetrahydroisoquinoline-3-carboxylate hydrochloride and 8 ml of triethylamine in 50 ml of chloroform which was cooled in an ice bath, there was carefully added N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl chloride hydrochloride obtained above. The reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was washed twice with 50 ml of saturated sodium chloride solution and evaporated to dryness. The residue was dissolved in water-ethanol and ajusted to pH 12 with 5N NaOH solution at a temperature below 0° C to precipitate a solid. This was collected by filtration to give 3 g of methyl 2-[N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate.

Workup

  1. customobtained above
  2. washThe reaction mixture was washed twice with 50 ml of saturated sodium chloride solution
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in water-ethanol
  5. customajusted to pH 12 with 5N NaOH solution at a temperature below 0° C
  6. customto precipitate a solid
  7. filtrationThis was collected by filtration

Sources & evidence

ORD record
ord-49b5163e1104467baab56ce5102838f7
Source dataset
uspto-grants-1978_08
Patent number
US04104392

Reaction notes

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