HCID 178477443, compound → HCID 178477444, compound

HRID 329002Notes

Reaction equation

HRID 329002 reaction equation
[N:1]#[N:2].C([O:7][C:8](=[O:44])[CH2:9][N:10]([C:16](=[O:43])[C@H:17]([CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:42])[NH2:41])[NH:18][S:19]([C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][C:26]([O:34][CH3:35])=[C:27]([O:32][CH3:33])[CH:28]=2)[CH:23]=1)(=[O:21])=[O:20])[CH2:11][CH2:12][S:13][CH2:14][CH3:15])(C)(C)C>FC(F)(F)C(O)=O>[N:1]#[N:2].[CH3:33][O:32][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:34][CH3:35])[CH:23]=[C:22]([S:19]([NH:18][C@H:17]([C:16]([N:10]([CH2:11][CH2:12][S:13][CH2:14][CH3:15])[CH2:9][C:8]([OH:44])=[O:7])=[O:43])[CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:41])[NH2:42])(=[O:21])=[O:20])[CH:31]=[CH:30]2

Participants

3

Reactant 1

HCID 178477443HCID 178477443, compound

Product 1

HCID 178477444HCID 178477444, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5.0 g of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl-N-(2-ethylthioethyl)glycine tert-butyl ester in 10 ml of trifluoroacetic acid 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 ethanol-H2O-NH4OH (5:4:1).

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 ethanol-H2O-NH4OH (5:4:1)

Sources & evidence

ORD record
ord-0b72bac40efa444eac47e69c5fc30de4
Source dataset
uspto-grants-1977_04
Patent number
US04018913

Reaction notes

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