Hydrochloric Acid → HCID 25139186, compound

HRID 1669113Notes

Reaction equation

HRID 1669113 reaction equation
[Si]([O:8][CH2:9][CH:10]1[CH2:25][C:24]2[C:12](=[CH:13][C:14]3[N+:19]([O-:20])=[N:18][C:17]([CH2:21][CH3:22])=[N:16][C:15]=3[CH:23]=2)[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO>[CH2:21]([C:17]1[N:18]=[N+:19]([O-:20])[C:14]2[CH:13]=[C:12]3[C:24]([CH2:25][CH:10]([CH2:9][OH:8])[CH2:11]3)=[CH:23][C:15]=2[N:16]=1)[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 25139185HCID 25139185, compound

Product 1

HCID 25139186HCID 25139186, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of silylether 135 (1.57 g, 4.37 mmol), and 1 N HCl (5 mL) in MeOH (40 mL) was stirred at 20° C. for 1 h. The solution was partitioned between EtOAc and water. The organic layer was dried, the solvent evaporated and the residue was purified by chromatography, eluting with a gradient (0-2%) of MeOH/DCM, to give alcohol 142 (0.84 g, 79%) as a yellow solid: mp (MeOH/EtOAc) 122-123° C.; 1H NMR [(CD3)2SO] δ 8.13 (s, 1H, H-9), 7.77 (s, 1H, H-5), 4.71 (t, J=5.2 Hz, 1H, OH), 3.42 (dd, J=6.4 Hz, 5.2 Hz, 2H, CH2O), 3.11-3.20 (m, 2H, CH2), 2.86-2.96 (m, 4H, CH2), 2.59-2.71 (m, 1H, H-7), 1.32 (t, J=7.5 Hz, 3H, CH3); 13C NMR [(CD3)2SO] δ 165.9, 153.9, 148.1, 146.8, 131.6, 122.5, 113.8, 63.5, 41.6, 35.3, 35.0, 29.6, 11.8. Anal. calcd for C13H15N3O2: C, 63.7; H, 6.2; N, 17.1. Found: C, 63.9; H, 6.2; N, 17.4%.

Workup

  1. customThe solution was partitioned between EtOAc and water
  2. customThe organic layer was dried
  3. customthe solvent evaporated
  4. customthe residue was purified by chromatography
  5. washeluting with a gradient (0-2%) of MeOH/DCM

Sources & evidence

ORD record
ord-48c1776c97224d91933e62944cb9294b
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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