Hydrochloric Acid → HCID 57722285, compound

HRID 1986547Notes

Reaction equation

HRID 1986547 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[C:18](=[O:19])[CH:17]([NH:20][C:21](=[O:40])[C@@H:22]([C@H:25]2[C@@H:30]([OH:31])[C@@H:29](/[CH:32]=[CH:33]/[C:34]([CH3:37])([CH3:36])[CH3:35])[O:28]C(C)(C)[O:26]2)[O:23][CH3:24])[CH2:16][S:15][CH2:14][CH2:13]1.Cl.[OH-].[Na+]>C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[C:18](=[O:19])[CH:17]([NH:20][C:21](=[O:40])[C@H:22]([O:23][CH3:24])[C@H:25]([OH:26])[C@@H:30]([OH:31])[C@H:29]([OH:28])/[CH:32]=[CH:33]/[C:34]([CH3:37])([CH3:35])[CH3:36])[CH2:16][S:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57722280HCID 57722280, compound

Product 1

HCID 57722285HCID 57722285, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40 mg of 44 (70 μmol) are mixed with 0.38 ml of THF and 0.75 ml of 1N hydrochloric acid, 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. 25 mg of expected product Example 16 are obtained (yield=67%).

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-ffc2ffe4942949e1a4bf6052737b99a1
Source dataset
uspto-grants-2009_06
Patent number
US07550453B2

Reaction notes

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