Hydrochloric Acid → HCID 67740879, compound

HRID 1654742Notes

Reaction equation

HRID 1654742 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:22][S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:18][C:19]([OH:21])=[O:20])=[O:15])=[CH:6][CH:5]=1.[CH2:32](O)[CH3:33].Cl>O1CCOCC1>[NH2:1][N:2]=[CH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:22][S:23]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)(=[O:24])=[O:25])[CH2:18][C:19]([O:21][CH2:32][CH3:33])=[O:20])=[O:15])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 70062045HCID 70062045, compound

Product 1

HCID 67740879HCID 67740879, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(±)-3-[[5-[4-(Aminoiminomethyl)phenyl]-1-oxopentyl]amino]-4-(phenylsulfonyl)butanoic acid (2.5 g) was added to dry ethanol (50 ml) and 4N HCl in dioxane (10 ml) . This mixture was left to stir for 2 h. After complete reaction the solvent was removed under reduced pressure and the oily mass was purified by reverse phase chromatography (water/acetonitrile) and lyophilized to give 1.6 g of the title compound as a white solid: 1H NMR (d6 -DMSO) δ1.15 (t, 3H, J=7.5 Hz), 1.48 (m, 2H), 1.56 (m, 2H), 1.75 (m, 2H), 2.10 (m, 2H), 2.41 (m, 2H), 2.68 (m, 2H), 3.9 (m, 1H), 4.0 (q, 2H, J=7.5 Hz), 4.02 (m, 2H), 7.35 (m, 9H), 7.7 (bd, 1H, J=7.9 Hz), 9.05 (bs, 2H), 9.3 (bs, 2H)MS (FAB) m/e 474.1 (M+H+)

Workup

  1. waitThis mixture was left
  2. customAfter complete reaction the solvent
  3. customwas removed under reduced pressure
  4. customthe oily mass was purified by reverse phase chromatography (water/acetonitrile)

Sources & evidence

ORD record
ord-5f54aebe6725424a8d25cf1b15f79993
Source dataset
uspto-grants-1995_04
Patent number
US05409939

Reaction notes

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