Sodium Bicarbonate → HCID 86757974, compound

HRID 843152Notes

Reaction equation

HRID 843152 reaction equation
[CH:1]1([CH2:7][C@@H:8]2[O:12][C:11]([C:13]3[O:14][C:15]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][CH2:26][N:27](C(OC(C)(C)C)=O)[CH2:28][C:29]5[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[C:16]=4[C:17]=3[CH3:18])=[N:10][C@H:9]2[C:42]([N:44]2[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]2)=[O:43])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O.ClCCl>[CH:1]1([CH2:7][C@@H:8]2[O:12][C:11]([C:13]3[O:14][C:15]4[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]5[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[C:16]=4[C:17]=3[CH3:18])=[N:10][C@H:9]2[C:42]([N:44]2[CH2:49][CH2:48][N:47]([CH3:50])[CH2:46][CH2:45]2)=[O:43])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86757973HCID 86757973, compound

Product 1

HCID 86757974HCID 86757974, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

dl-[5-Cyclohexylmethyl-2-(3-methyl-4-{3-[tert-butoxycarbonyl-(pyridin-3-ylmethyl)-amino]-propoxy}-benzofuran-2-yl)-trans-4,5-dihydro-oxazol-4-yl]-(4-methyl-piperazin-1-yl)-methanone (11.9 mg) was dissolved in 1:1 mixture of trifluoroacetic acid and dichloromethane (1 ml) and was allowed to stand at room temperature for 45 minutes. The resulted solution was poured into saturated aqueous sodium bicarbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. After evaporation of the solvent the crude product was purified by silica gel column chromatography (Fuji Silysia, DU-3050) using 1000:10:1 mixture of dichloromethane, methanol and triethylamine as an eluent to give the title compound (7.7 mg) as a white solid. FAB-MS: m/z 588 (MH+); NMR (CDCl3): δ 0.9-2.0 (13H, m), 2.06 (2H, quintet, J=6.27 Hz), 2.34 (3H, s), 2.43 (2H, t, J=4.95 Hz), 2.55 (2H, m), 2.62 (3H, s), 2.89 (2H, t, J=6.93 Hz), 3.70 (2H, m), 3.81 (1H, m), 3.84 (2H, s), 4.07 (1H, m), 4.16 (2H, t, J=5.93 Hz), 4.55 (1H, d, J=6.60 Hz), 5.54 (1H, m), 6.61 (1H, d, J=7.92 Hz), 7.10 (1H, d, J=8.25 Hz), 7.15-7.30 (2H, m), 7.67 (1H, dt, J=7.92 Hz, 1.98 Hz), 8.49 (1H, dd, J=1.65 Hz, 4.95 Hz), 8.57 (1H, d, J=1.98 Hz).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customAfter evaporation of the solvent the crude product
  5. customwas purified by silica gel column chromatography (Fuji Silysia, DU-3050)
  6. addition1000:10:1 mixture of dichloromethane, methanol and triethylamine as an eluent

Sources & evidence

ORD record
ord-54ede3c209604374af40d0179ff22ff6
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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