Lithium Hydroxide → HCID 70061469, compound

HRID 2225977Notes

Reaction equation

HRID 2225977 reaction equation
Cl.[NH2:2][N:3]=[CH:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:7][CH:6]=1.[NH2:19][C:20]1C(O)=C[O:22][CH:21]=1.O[Li].O.[Li+].[OH-].[C:31]([C:35]([OH:37])=[O:36])(F)(F)F>O>[NH2:2][N:3]=[CH:4][C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:18])[CH2:13][CH2:14][C:15]([NH:19][C@H:20]([CH2:21][OH:22])[CH2:31][C:35]([OH:37])=[O:36])=[O:17])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 218347004-Aminofuran-3-olHCID 699519434-[(4-(Aminoiminomethyl)phenyl)amino]-4-oxobutanoic acid hydrochloride

Product 1

HCID 70061469HCID 70061469, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The lactone derivative prepared as usual by coupling of 4-[[4-(aminoiminomethyl)phenyl]amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 and 3-amino-4hydroxyfuran was dissolved in water (20 mL) and the pH adjusted to 10.5 by addition of LiOH H2O. The reaction was allowed to proceed at room temperature for 2 hours and the product isolated by RPHPLC. The appropriate fractions were adjusted to pH 7 by addition of LiOH prior to solvent removal. Subsequent lyophilization gave a white solid: 1H NMR (d6DMSO) δ 2.5 (m, 6H), 2.9 (m, 1H), 4.08 (m, 1H ), 4.42 (m, 2H ), 7.80 (s, 4H), 8.5 (d, 1H), 8.85 (s, 2H), 9.15 (s, 2H), 10.4 (s, 1H). MS (FAB) 337.1 (MH+), 319.2 (M-H2O+H). Elemental analysis; Required for C15H20N4O5. CF3CO2H 1.5 H2O: C 42.77 H 5.07 N 11.74 Found: C 43.06 H 4.24 N 11.45

Workup

  1. customthe product isolated by RPHPLC
  2. customto solvent removal
  3. customSubsequent lyophilization gave a white solid

Sources & evidence

ORD record
ord-2661114cfe894a949ad9b0d31e3d8faa
Source dataset
uspto-grants-1994_09
Patent number
US05344957

Reaction notes

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