Water → 2-(4-chloro-N-(pent-1-yn-3-yl)phenylsulfonamido)-butanoic acid

HRID 15726Notes

Reaction equation

HRID 15726 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH:17]([CH2:22][CH3:23])[C:18]([O:20]C)=[O:19])[CH:12]([CH2:15][CH3:16])[C:13]#[CH:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.O.[OH-].[Li+].O>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH:17]([CH2:22][CH3:23])[C:18]([OH:20])=[O:19])[CH:12]([CH2:15][CH3:16])[C:13]#[CH:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59342372methyl 2-(4-chloro-N-(pent-1-yn-3-yl)phenylsulfonamido)butanoate

Product 1

HCID 593423732-(4-chloro-N-(pent-1-yn-3-yl)phenylsulfonamido)-butanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound 59 (584 mg, 163 mmol) was dissolved in THF (10 mL). Lithium hydroxide monohydrate (134 mg, 2.0 eq) was added followed by 10 mL of water. The mixture was stirred at room temperature overnight. The solvent was removed and the solution was adjusted to pH 3-4 using 3N HCl, The mixture was then extracted with EtOAc (4×20 mL). The combined organic layers were washed with brine and dried (MgSO4). After removal of the solvent a white solid was obtained as the product 60. LCMS 366.0 (M+23).

Workup

  1. customThe solvent was removed
  2. extractionThe mixture was then extracted with EtOAc (4×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. customAfter removal of the solvent a white solid

Sources & evidence

ORD record
ord-280224407b1946e5a730190361d3df97
Source dataset
uspto-grants-2010_06
Patent number
US07732609B2

Reaction notes

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