Hydrochloric Acid → HCID 57734091, compound

HRID 1037730Notes

Reaction equation

HRID 1037730 reaction equation
[Cl:1][C@H:2]1[C@H:6]([CH2:7][CH2:8][CH2:9][C:10]2[S:14][C:13]([C:15]([O:17]C)=[O:16])=[CH:12][CH:11]=2)[C@@H:5](/[CH:19]=[CH:20]/[C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][C@@H:25]([OH:27])[CH3:26])[C@H:4]([OH:29])[CH2:3]1.[OH-].[Li+].Cl>C1COCC1>[Cl:1][C@H:2]1[C@H:6]([CH2:7][CH2:8][CH2:9][C:10]2[S:14][C:13]([C:15]([OH:17])=[O:16])=[CH:12][CH:11]=2)[C@@H:5](/[CH:19]=[CH:20]/[C@@H:21]([OH:28])[CH2:22][CH2:23][CH2:24][C@@H:25]([OH:27])[CH3:26])[C@H:4]([OH:29])[CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57734126HCID 57734126, compound

Product 1

HCID 57734091HCID 57734091, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 40 mg of ester 16 (0.09 mmol) in 0.72 mL of THF was hydrolyzed with 360 uL of aqueous lithium hydroxide (0.5M, 0.18 mmol)) at 23° C. for 16 h. The mixture was acidified by addition of 1N HCl and then extracted with EtOAc (2×). The combined organic portions were washed with brine (2×), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to yield 23.3 mg (60%) of the free acid 17.

Workup

  1. customat 23° C.
  2. customfor 16 h
  3. extractionextracted with EtOAc (2×)
  4. washThe combined organic portions were washed with brine (2×)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76c5f10345a34d3bb4be8cc628059a93
Source dataset
uspto-grants-2013_10
Patent number
US08546603B2

Reaction notes

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