Hydrochloric Acid → HCID 57722289, compound

HRID 1986548Notes

Reaction equation

HRID 1986548 reaction equation
[CH3:1][C:2]([CH3:39])([CH3:38])/[CH:3]=[CH:4]/[C@H:5]1[O:10]C(C)(C)[O:8][C@@H:7]([C@@H:13]([O:35][CH3:36])[C:14]([NH:16][CH:17]2[CH2:23][N:22]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:21][CH2:20][NH:19][C:18]2=[O:34])=[O:15])[C@H:6]1[OH:37].Cl.[OH-].[Na+]>C1COCC1>[O:34]=[C:18]1[CH:17]([NH:16][C:14](=[O:15])[C@H:13]([O:35][CH3:36])[C@H:7]([OH:8])[C@@H:6]([OH:37])[C@H:5]([OH:10])/[CH:4]=[CH:3]/[C:2]([CH3:39])([CH3:1])[CH3:38])[CH2:23][N:22]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][CH2:20][NH:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57722304HCID 57722304, compound

Product 1

HCID 57722289HCID 57722289, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

81 mg of 49 (148 μmol) are mixed with 0.75 ml of THF and 1.5 ml of 1N hydrochloric acid (750 μmol), 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 2 ml of EtOAc. The organic phases are combined, dried over magnesium sulfate and filtered, and then evaporated to dryness. 49 mg of expected product Example 18 are obtained (yield=66%).

Workup

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

Sources & evidence

ORD record
ord-4cf8fff9ff8f4011a5096d3e274fb8e9
Source dataset
uspto-grants-2009_06
Patent number
US07550453B2

Reaction notes

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