Hydrochloric Acid → HCID 118037132, compound

HRID 628932Notes

Reaction equation

HRID 628932 reaction equation
[OH-].[Li+].[Cl:3][C@H:4]1[C@H:8]([CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([C:17]([O:19]C)=[O:18])=[CH:14][CH:13]=2)[C@@H:7](/[CH:21]=[CH:22]/[C@@H:23]([OH:30])[CH2:24][CH:25]([OH:29])[CH2:26][CH2:27][CH3:28])[C@H:6]([OH:31])[CH2:5]1.Cl>O.C1COCC1>[Cl:3][C@H:4]1[C@H:8]([CH2:9][CH2:10][CH2:11][C:12]2[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=2)[C@@H:7](/[CH:21]=[CH:22]/[C@@H:23]([OH:30])[CH2:24][CH:25]([OH:29])[CH2:26][CH2:27][CH3:28])[C@H:6]([OH:31])[CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118036993HCID 118036993, compound

Product 1

HCID 118037132HCID 118037132, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (0.32 mL of a 0.5N solution in H2O, 0.16 mmol) was added to a solution of the ester 13 (36 mg, 0.081 mmol) in THF (0.64 mL) at 23° C. After stirring for 24 h the reaction mixture was acidified with 1N HCl and extracted with EtOAc. The organic portion was washed with brine (2×), dried (Na2SO4), filtered and concentrated in vacuo to provide 27.6 mg (79%) of the free acid 14 (see Scheme 1).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic portion was washed with brine (2×)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acbeb576b3424987a07258271f6708fd
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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