HCID 178496913, compound → HCID 178486634, compound

HRID 2419032Notes

Reaction equation

HRID 2419032 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH:38]([C:39]([O:41]C)=[O:40])[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]1)=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16])[CH:7]=[CH:6]2>CO.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]=[C:8]([S:15]([NH:18][C@H:19]([C:27]([N:29]1[CH:38]([C:39]([OH:41])=[O:40])[CH2:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30]1)=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])(=[O:16])=[O:17])[CH:7]=[CH:6]2

Participants

4

Reactant 1

HCID 178496913HCID 178496913, compound

Product 1

HCID 178486634HCID 178486634, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3 g of methyl 2-[N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylate in 15 ml of methanol and 5 ml of 2N NaOH solution was warmed to 50° C and held at that temperature for 15 hours. At the end of this period, the reaction mixture was concentrated and chromatographed on 200 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited) packed in water, washed with ethanol-water (1:4) and eluted with ethanol-water-NH4OH (10:9:1). The main fraction was evaporated to dryness and washed with ether to give 1.6 g of 2-[N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.

Workup

  1. concentrationAt the end of this period, the reaction mixture was concentrated
  2. customchromatographed on 200 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited)
  3. washwashed with ethanol-water (1:4)
  4. washeluted with ethanol-water-NH4OH (10:9:1)
  5. customThe main fraction was evaporated to dryness
  6. washwashed with ether

Sources & evidence

ORD record
ord-04955e7175e14413ae8c8bc1b2069d18
Source dataset
uspto-grants-1978_08
Patent number
US04104392

Reaction notes

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