Sodium Hydroxide → HCID 57649542, compound

HRID 2421857Notes

Reaction equation

HRID 2421857 reaction equation
[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][CH2:11][C@H:10]([NH:19][C:20](=[O:39])[C@@H:21]([C@H:24]2[C@@H:29]([OH:30])[C@@H:28](/[CH:31]=[CH:32]/[C:33]([CH3:36])([CH3:35])[CH3:34])[O:27]C(C)(C)[O:25]2)[O:22][CH3:23])[C:9]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.Cl>[CH2:1]([N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][CH2:11][C@H:10]([NH:19][C:20](=[O:39])[C@H:21]([O:22][CH3:23])[C@H:24]([OH:25])[C@@H:29]([OH:30])[C@H:28]([OH:27])/[CH:31]=[CH:32]/[C:33]([CH3:35])([CH3:36])[CH3:34])[C:9]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57649587HCID 57649587, compound

Product 1

HCID 57649542HCID 57649542, compoundYield 17.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

101 mg of 9 (178 μmol) in 0.85 mL of THF and 1.78 mL of 1N hydrochloric acid are mixed together, with stirring and under argon, in a 20 mL round-bottomed flask. Stirring is continued for 5 hours at room temperature. The solution is then cooled to 0° C. It is neutralized to pH 7.0 with 1N sodium hydroxide. The resulting mixture is extracted twice with 5 mL of EtOAc. The organic phases are combined, dried over magnesium sulfate and filtered and then brought to dryness. 66 mg of crude product are obtained, which product, after purification on a preparative silica plate (eluent: 90/10 CH2Cl2/MeOH), gives 16.5 mg of expected product Example 3.

Workup

  1. stirringStirring
  2. extractionThe resulting mixture is extracted twice with 5 mL of EtOAc
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. custom66 mg of crude product are obtained
  6. customwhich product, after purification on a preparative silica plate (eluent: 90/10 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-189b29c299014de797e9503fed25daf6
Source dataset
uspto-grants-2011_06
Patent number
US07960373B2

Reaction notes

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