Gluconic Acid → HCID 70031375, compound

HRID 1862061Notes

Reaction equation

HRID 1862061 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C@@H:6]([NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[CH2:7]2.[O:34]=[C:35]([OH:46])[C@@H:36]([C@H:38]([C@@H:40]([C@@H:42]([CH2:44][OH:45])[OH:43])[OH:41])[OH:39])[OH:37]>C(O)C>[O:34]=[C:35]([OH:46])[C@@H:36]([C@H:38]([C@@H:40]([C@@H:42]([CH2:44][OH:45])[OH:43])[OH:41])[OH:39])[OH:37].[CH2:1]([C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C@@H:6]([NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[CH2:7]2)[CH3:35]

Participants

4

Reactant 2

HCID 10690Gluconic AcidHCID 9846516AR-A000002

Product 1

HCID 70031375HCID 70031375, compoundYield 120.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide (100 mg, 0.22 mmmol) was dissolved in ethanol (3 mL) and a 50% aqueous D-gluconic acid solution (80 μL, 0.24 mmol) was added dropwise. The solvent was removed in vacuo to give a white viscous oil. The crude oil was recrystallized from a 5% H2O in acetone solution (3 mL) and a 10% H2O in acetone solution (3 mL), decanted, then allowed to stand at room temperature for 65 h. The solid was filtered and washed with a cold 3% H2O in acetone solution to give 95 mg (65% yield) of a white solid: nip 130-140° C. Anal. Calcd. for C27H36N4O2xC6H12O7xH2O: C, 59.8; H, 7.6; N, 8.5. Found: C, 60.0; H, 7.4; N, 8.3.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a white viscous oil
  3. customThe crude oil was recrystallized from a 5% H2O in acetone solution (3 mL)
  4. customa 10% H2O in acetone solution (3 mL), decanted
  5. filtrationThe solid was filtered
  6. washwashed with a cold 3% H2O in acetone solution

Sources & evidence

ORD record
ord-c83b3c1b465a41b6ba4e82dfd754992b
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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