Tetrahydrofuran → HCID 20592607, compound

HRID 1369259Notes

Reaction equation

HRID 1369259 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[CH2:22][C@@H:21]([CH2:23][C:24]([O:26]CC)=[O:25])[C:20]4[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=4[CH2:18][C:17]=3[CH:33]=2)[CH:3]=1.O[Li].O.C1COCC1>O>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]3[CH2:22][C@@H:21]([CH2:23][C:24]([OH:26])=[O:25])[C:20]4[CH:29]=[CH:30][CH:31]=[CH:32][C:19]=4[CH2:18][C:17]=3[CH:33]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54419804HCID 54419804, compound

Product 1

HCID 20592607HCID 20592607, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl (S)-10,11-dihydro-3-[3-(4-aminopyridin-2-ylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (2.4 g, 5 mmole), LiOH.H2O (0.3 g, 7 mmole), THF (30 mL), and H2O (10 mL) was stirred at RT for 48 hr, then was concentrated. The residue was diluted with H2O and extracted with Et2O. The Et2O layers were discarded. The aqueous layer was stirred with gentle warming under vacuum to remove residual organic solvents, then was filtered. The resulting aqueous solution was stirred at RT while the pH was slowly and carefully adjusted to 5.5-6.0 with 1.0 N HCl The mixture was stirred for 0.5 hr, then the solid was collected by suction filtration and washed with plenty of H2O. Drying in high vacuum at 60° C. gave the title compound (1.0 g, 42%) as a glassy solid: MS (ES) m/e 417.7 (M+H)+. Anal. Calcd for C25H27N3O3 1.4 HCl (468.554): C, 64.08; H, 6.11; N, 8.97. Found: C, 64.16; H, 6.20; N, 8.71.

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with H2O
  3. extractionextracted with Et2O
  4. stirringThe aqueous layer was stirred
  5. temperaturewith gentle warming under vacuum
  6. customto remove residual organic solvents
  7. filtrationwas filtered
  8. stirringThe resulting aqueous solution was stirred at RT while the pH
  9. stirringwas stirred for 0.5 hr
  10. filtrationthe solid was collected by suction filtration
  11. washwashed with plenty of H2O
  12. customDrying in high vacuum at 60° C.

Sources & evidence

ORD record
ord-38736e5cd8f74d07a61e6be98e03b1f6
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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