Acetic Acid → HCID 25227444, compound

HRID 1619486Notes

Reaction equation

HRID 1619486 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][C:5]1[C:6]2[CH:29]=[CH:28][C:27]([Cl:30])=[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.O.[Li+].[OH-].CC(O)=O>C1COCC1.[Cl-].[Na+].O>[Cl:30][C:27]1[CH:28]=[CH:29][C:6]2[C:5]([CH2:4][C:3]([OH:31])=[O:2])=[C:13]3[N:8]([C:7]=2[N:26]=1)[CH2:9][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])[CH2:11][CH2:12]3

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 59471429HCID 59471429, compound

Product 1

HCID 25227444HCID 25227444, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 20 mg of (±)-{2-chloro-8-[(4-fluoro-benzenesulfonyl)-methyl-amino]-6,7,8,9-tetrahydro-pyrido[3,2-b]indolizin-5-yl}-acetic acid methyl ester in 1.2 mL of THF was added 1.5 mL of water, followed by 0.2 mL of 1 N aqueous LiOH solution. The mixture was stirred for 1 h at room temperature and 0.1 mL of AcOH was added, followed by 3 mL of brine. The mixture was extracted with 2×10 mL of EtOAc and the combined extracts was dried over Na2SO4 and concentrated to give 18 mg of the desired product as a white solid.

Workup

  1. extractionThe mixture was extracted with 2×10 mL of EtOAc
  2. dry with materialthe combined extracts was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ce93b579a37a48c1a2caff3334be9e7d
Source dataset
uspto-grants-2014_07
Patent number
US08772312B2

Reaction notes

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