Hydrochloric Acid → HCID 11697866, compound

HRID 1986549Notes

Reaction equation

HRID 1986549 reaction equation
[CH3:1][C:2]([CH3:33])([CH3:32])/[CH:3]=[CH:4]/[C@H:5]1[O:10]C(C)(C)[O:8][C@@H:7]([C@@H:13]([O:29][CH3:30])[C:14]([NH:16][CH:17]2[C:23](=[O:24])[NH:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[S:19][CH2:18]2)=[O:15])[C@H:6]1[OH:31].Cl.[OH-].[Na+]>C1COCC1>[O:24]=[C:23]1[NH:22][C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[S:19][CH2:18][CH:17]1[NH:16][C:14](=[O:15])[C@H:13]([O:29][CH3:30])[C@H:7]([OH:8])[C@@H:6]([OH:31])[C@H:5]([OH:10])/[CH:4]=[CH:3]/[C:2]([CH3:33])([CH3:1])[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57722255HCID 57722255, compound

Product 1

HCID 11697866HCID 11697866, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

78 mg of 51 (163 μmol) are mixed with 0.8 ml of THF and 1.6 ml of 1N hydrochloric acid (1.6 mmol), with stirring and under argon. Stirring is continued for 5 hours at room temperature. The solution is then cooled to 0° C. and neutralized to pH 7.0 with 1N sodium hydroxide. The mixture is extracted twice with 5 ml of EtOAc. The organic phases are combined, dried over magnesium sulfate and filtered, and then evaporated to dryness. 19.5 mg of expected product Example 19 are obtained (yield=27%).

Workup

  1. stirringStirring
  2. extractionThe mixture is extracted twice with 5 ml of EtOAc
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-2d722e67fa484af39c854dbb2b1ee6ed
Source dataset
uspto-grants-2009_06
Patent number
US07550453B2

Reaction notes

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