Hydrochloric Acid → HCID 25234654, compound

HRID 1924450Notes

Reaction equation

HRID 1924450 reaction equation
[C:1]([C:5]1[C:6]([O:36][CH3:37])=[C:7]([CH:25]=[C:26]([N:28]2[CH:33]=[CH:32][C:31](=[O:34])[NH:30][C:29]2=[O:35])[CH:27]=1)/[CH:8]=[CH:9]/[C:10]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][C:11]=1[C:12]([O:14]C)=[O:13])([CH3:4])([CH3:3])[CH3:2].Cl>C1COCC1.[OH-].[Na+]>[C:1]([C:5]1[C:6]([O:36][CH3:37])=[C:7]([CH:25]=[C:26]([N:28]2[CH:33]=[CH:32][C:31](=[O:34])[NH:30][C:29]2=[O:35])[CH:27]=1)/[CH:8]=[CH:9]/[C:10]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])=[CH:16][C:11]=1[C:12]([OH:14])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 25234656HCID 25234656, compound

Product 1

HCID 25234654HCID 25234654, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of the product from Example 25 (55 mg, 0.104 mmol) in THF (1 ml) and 1N aq. NaOH (1 ml) was stirred in the dark at room temperature for 1.5 h. 1N aqueous HCl was added until pH 3, and the resulting mixture was extracted with EtOAc (2×2 ml). The combined organic layers were dried over Na2SO4, filtered and concentrated to give the title compound (53 mg, 99%). 1H NMR (300 MHz, DMSO-d6) δ 13.22 (br s, 1 H) 11.40 (d, J=2.21 Hz, 1 H) 10.02 (s, 1 H) 7.72-7.91 (m, 3 H) 7.68 (d, J=2.57 Hz, 1H) 7.49 (d, J=2.57 Hz, 1 H) 7.42 (dd, J=8.64, 2.39 Hz, 1 H) 7.21 (d, J=2.57 Hz, 1 H) 7.16 (d, J=16.18 Hz, 1 H) 5.64 (dd, J=7.72, 2.21 Hz, 1 H) 3.79 (s, 3 H) 3.04 (s, 3 H) 1.38 (s, 9 H).

Workup

  1. extractionthe resulting mixture was extracted with EtOAc (2×2 ml)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5ff17bceb5534c0daedc1606d14cb72d
Source dataset
uspto-grants-2012_05
Patent number
US08178548B2

Reaction notes

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