Hydrochloric Acid → HCID 69084156, compound

HRID 1396304Notes

Reaction equation

HRID 1396304 reaction equation
[F:1][C@@H:2]([C@@H:4]1[C@@H:15]2[C@H:11]([O:12]C(C)(C)[O:14]2)[C@@H:10]2[C@@H:6]([S:7][C:8]([N:18]([CH3:20])[CH3:19])=[N:9]2)[O:5]1)[CH3:3].Cl.[NH4+].[OH-]>CO>[CH3:20][N:18]([CH3:19])[C:8]1[S:7][C@H:6]2[O:5][C@H:4]([C@H:2]([F:1])[CH3:3])[C@@H:15]([OH:14])[C@H:11]([OH:12])[C@H:10]2[N:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 69280794HCID 69280794, compound

Product 1

HCID 69084156HCID 69084156, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 159 (150 mg, 0.16 mmol) in methanol (10 mL) was treated with concentrated aqueous HCl (1 mL) for 1 hour at room temperature, then the resulting solution was concentrated under vacuum to give a residue, which was dissolved into methanol (5 mL) and neutralized with concentrated NH4OH (1 mL). After removal of all the solvent, the residue was purified by flash column chromatography with 10% methanol in dichloromethane to afford the title compound as a white solid (50.1 mg, 38%). (ES, m/z); [M+H]+ 265.0; 1H NMR (300 MHz, D2O) δ 6.23 (d, J=6.6 Hz, 1H), 4.97-4.70 (m, 1H), 4.22-4.19 (m, 1H), 4.02-3.99 (m, 1H), 3.67-3.62 (m, 2H), 2.91 (s, 6H), 1.26 (dd, J=6.6 Hz, 26.1 Hz, 3H).

Workup

  1. concentrationthe resulting solution was concentrated under vacuum
  2. customto give a residue, which
  3. customAfter removal of all the solvent
  4. customthe residue was purified by flash column chromatography with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-53333fd5383947b6b43bcf3d6546a1c3
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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