Hydrogen chloride-ethyl acetate → HCID 178486643, compound

HRID 1834198Notes

Reaction equation

HRID 1834198 reaction equation
[N:1]#[N:2].S(S(O)=O)(O)=O.C([O:13][C:14](=[O:52])[CH2:15][N:16]([C:24](=[O:51])[C@H:25]([CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:50])[NH2:49])[NH:26][S:27]([C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][C:34]([O:42][CH3:43])=[C:35]([O:40][CH3:41])[CH:36]=2)[CH:31]=1)(=[O:29])=[O:28])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(C)(C)C.Cl.C(OCC)(=O)C>C(Cl)(Cl)Cl>[N:1]#[N:2].[CH3:41][O:40][C:35]1[CH:36]=[C:37]2[C:32](=[CH:33][C:34]=1[O:42][CH3:43])[CH:31]=[C:30]([S:27]([NH:26][C@H:25]([C:24]([N:16]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:15][C:14]([OH:52])=[O:13])=[O:51])[CH2:44][CH2:45][CH2:46][NH:47][C:48](=[NH:49])[NH2:50])(=[O:29])=[O:28])[CH:39]=[CH:38]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178486644HCID 178486644, compound

Product 1

HCID 178486643HCID 178486643, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.00 g of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-benzylglycine tert-butyl ester hydrosulfite in 20 ml of chloroform was added 50 ml of 15% HCl-ethyl acetate. The reaction mixture was stirred for 5 hours at room temperature. At the end of this period, the reaction mixture was evaporated to dryness. The residue was washed several times with dry diethyl ether and chromatographed on 80 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited) packed in water, washed with water and eluted with 3% ammonium hydroxide solution. The fraction eluted from 3% ammonium hydroxide solution was evaporated to dryness to give 1.20 g (70 percent) of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-benzylglycine as an amorphous solid, I.R. (KBr): 3,370, 3,200, 1.615 cm-1.

Workup

  1. customAt the end of this period, the reaction mixture was evaporated to dryness
  2. washThe residue was washed several times with dry diethyl ether
  3. customchromatographed on 80 ml of Daiaion® SK 102 ion exchange resin (200-300 mesh, H+ form, manufactured by Mitsubishi Chemical Industries Limited)
  4. washwashed with water
  5. washeluted with 3% ammonium hydroxide solution
  6. washThe fraction eluted from 3% ammonium hydroxide solution
  7. customwas evaporated to dryness

Sources & evidence

ORD record
ord-d3d532daac044f4e9c52d208f1fc7b58
Source dataset
uspto-grants-1978_01
Patent number
US04069318

Reaction notes

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