Hydrochloric Acid → HCID 19084702, compound

HRID 962485Notes

Reaction equation

HRID 962485 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH2:14][O:15][C:16]([C:30]2[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=2)([C:26](OC)=[O:27])[CH2:17][O:18]CC2C=CC=CC=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[BH4-].[Li+].[ClH:52]>O1CCCC1>[ClH:52].[C:44]1([C:11]2([CH2:14][O:15][C:16]([C:30]3[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=[C:32]([C:40]([F:43])([F:41])[F:42])[CH:31]=3)([CH2:26][OH:27])[CH2:17][OH:18])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 19084691HCID 19084691, compound

Product 1

HCID 19084702HCID 19084702, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

The oil from step (a) above was dissolved in anhydrous tetrahydrofuran (50 ml) and lithium borohydride (0.140 g, 6.5 mmol) was added. The reaction was stirred at 25° C. for 30 minutes and quenched with saturated aqueous ammonium chloride solution (75 ml) and extracted into ethyl acetate (75 ml). The organic layer was dried over (MgSO4) and removed in vacuo. The residue was dissolved in ethanol (15 ml) and hydrogenated at 50 psi over Pd(OH)2 (0.150 g) for 16 h. The catalyst was filtered and the solvent evaporated. The residue was chromatographed on silica eluting with ethyl acetate. The oil obtained was treated with ethereal HCl and left standing for 16 h. The solid formed was filtered off and washed with ether to obtain the title compound. 1H NMR (DMSO-d6) δ 7.99 (1 H, s), 7.75 (2H, s), 7.48 (4H, m), 7.35 (1H. m), 3.85 (4H, s), 3.47 (2H, s), 3.33 (2H, br d), 2.97 (2H, br t), 2.56 (2H, br d), 2.10 (2H, br t). MS (Cl+) 478 [M+H]+.

Workup

  1. customquenched with saturated aqueous ammonium chloride solution (75 ml)
  2. extractionextracted into ethyl acetate (75 ml)
  3. dry with materialThe organic layer was dried over (MgSO4)
  4. customremoved in vacuo
  5. dissolutionThe residue was dissolved in ethanol (15 ml) and hydrogenated at 50 psi over Pd(OH)2 (0.150 g) for 16 h
  6. filtrationThe catalyst was filtered
  7. customthe solvent evaporated
  8. customThe residue was chromatographed on silica eluting with ethyl acetate
  9. customThe oil obtained
  10. waitleft
  11. waitstanding for 16 h
  12. customThe solid formed
  13. filtrationwas filtered off
  14. washwashed with ether

Sources & evidence

ORD record
ord-5f302373d50644c4b9bafd4c202c8473
Source dataset
uspto-grants-1998_06
Patent number
US05760018

Reaction notes

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