Glycolic Acid → HCID 70245399, compound

HRID 1596195Notes

Reaction equation

HRID 1596195 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.[C:34]([OH:38])(=[O:37])[CH2:35][OH:36]>C(O)C>[C:34]([OH:38])(=[O:37])[CH2:35][OH:36].[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

Participants

4

Reactant 2

HCID 757Glycolic AcidHCID 9846516AR-A000002

Product 1

HCID 70245399HCID 70245399, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a hot solution of (R)-N-[5-methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl)-4-morpholinobenzamide (1.0 g, 2.2 mmol) in ethanol (50 mL) was added a hot solution of glycolic acid (200 mg, 2.6 mmol) in ethanol (10 mL). The solvent was concentrated in vacuo and to the remaining solution (20 mL) was boiling ethyl acetate added until the solution was cloudy. After boiling for a few minutes, the solution was cooled and put in the refrigerator over night. The crystals were filtered and dried in vacuo to give 1.0 gram (83% yield) of the title compound as white crystals. Anal. Calcd. for C27H36N4O2×C7H6O3×2H2O: C, 62.1; H, 7.9; N, 10.0. Found: C, 62.7; H, 7.7; N, 9.6.

Workup

  1. concentrationThe solvent was concentrated in vacuo and to the remaining solution (20 mL)
  2. additionadded until the solution
  3. waitAfter boiling for a few minutes
  4. temperaturethe solution was cooled
  5. waitput in the refrigerator over night
  6. filtrationThe crystals were filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-43bc860da07e4c6d95dd549c21b30e60
Source dataset
uspto-grants-2001_09
Patent number
US06291458B1

Reaction notes

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