Acetic Acid → HCID 59471427, compound

HRID 1619487Notes

Reaction equation

HRID 1619487 reaction equation
C[O:2][C:3](=[O:30])[CH2:4][C:5]1[C:6]2[CH:29]=[CH:28][CH:27]=[N:26][C:7]=2[N:8]2[C:13]=1[CH2:12][CH2:11][CH:10]([N:14]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[CH3:15])[CH2:9]2.C1COCC1.O.[Li+].[OH-].CC(O)=O>[Cl-].[Na+].O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([N:14]([CH3:15])[CH:10]2[CH2:11][CH2:12][C:13]3[N:8]([C:7]4[N:26]=[CH:27][CH:28]=[CH:29][C:6]=4[C:5]=3[CH2:4][C:3]([OH:30])=[O:2])[CH2:9]2)(=[O:17])=[O:18])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 59471440(+/-)-{8-[(4-Fluoro-benzenesulfonyl)-methyl-amino]6,7,8,9-tetrahydro-pyrido[3,2-b]indolizin-5-yl}-acetic acid methyl ester

Product 1

HCID 59471427HCID 59471427, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (±)-{8-[(4-fluoro-benzenesulfonyl)-methyl-amino]6,7,8,9-tetrahydro-pyrido[3,2-b]indolizin-5-yl}-acetic acid methyl ester (28 mg) in 4 mL of 121 THF/water was added 0.2 mL of 1 N aqueous LiOH solution. After stirring for 1 h at room temperature, AcOH (0.2 mL) and 4 mL of brine were added and the mixture was extracted with 2×10 mL of EA, dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography eluted with 50% EtOAc/hexane containing 5% AcOH to give 20 mg of the desired product as a white solid.

Workup

  1. extractionthe mixture was extracted with 2×10 mL of EA
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration and concentration
  4. customthe residue was purified by silica gel chromatography
  5. washeluted with 50% EtOAc/hexane containing 5% AcOH

Sources & evidence

ORD record
ord-36cb9c5f548b42c983114a71df6bf092
Source dataset
uspto-grants-2014_07
Patent number
US08772312B2

Reaction notes

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