HCID 178487530, compound → HCID 178487529, compound

HRID 259243Notes

Reaction equation

HRID 259243 reaction equation
[N:1]#[N:2].C([O:7][C:8](=[O:43])[CH2:9][N:10]([C:17](=[O:42])[C@H:18]([CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:41])[NH2:40])[NH:19][S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[CH:28][CH:29]=2)[CH:24]=1)(=[O:22])=[O:21])[CH2:11][CH:12]1[O:16][CH2:15][CH2:14][CH2:13]1)(C)(C)C>FC(F)(F)C(O)=O>[N:1]#[N:2].[CH3:34][O:33][C:27]1[CH:26]=[C:25]2[C:30]([CH:31]=[CH:32][C:23]([S:20]([NH:19][C@H:18]([C:17]([N:10]([CH2:11][CH:12]3[O:16][CH2:15][CH2:14][CH2:13]3)[CH2:9][C:8]([OH:43])=[O:7])=[O:42])[CH2:35][CH2:36][CH2:37][NH:38][C:39](=[NH:40])[NH2:41])(=[O:21])=[O:22])=[CH:24]2)=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 178487530HCID 178487530, compound

Product 1

HCID 178487529HCID 178487529, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 4.8 g of N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl-N-tetrahydrofurfurylglycine 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 300 ml of Daiaion® SA 10A ion exchange resin (100-200 mesh, OH- form, manufactured by Mitsubishi Chemical Industries Limited) packed in water, washed with 50% ethanol-water and eluted with ethanol-water-acetic acid solution (5:4:1). The main fraction eluted from the ethanol-water-acetic acid solution was evaporated to dryness to give a gummy material. This was recrystallized from ethanol-water to give 2.8 g of N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl-N-tetrahydrofurfurylglycine in the form of a powder.

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 300 ml of Daiaion® SA 10A ion exchange resin (100-200 mesh, OH- form, manufactured by Mitsubishi Chemical Industries Limited)
  4. washwashed with 50% ethanol-water
  5. washeluted with ethanol-water-acetic acid solution (5:4:1)
  6. washThe main fraction eluted from the ethanol-water-acetic acid solution
  7. customwas evaporated to dryness
  8. customto give a gummy material
  9. customThis was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-b0892914867746c3b7d1a663f7a2c9e3
Source dataset
uspto-grants-1977_07
Patent number
US04036955

Reaction notes

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