Water → HCID 22645084, compound

HRID 1976410Notes

Reaction equation

HRID 1976410 reaction equation
[OH-:1].[Na+].C(OC(=O)CNC[S:12]([C:15]1[CH:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=1)(=[O:14])=[O:13])(C)(C)C.[C:23]([OH:27])#[C:24][CH2:25][CH3:26].[OH2:28]>>[CH2:23]([O:27][C:18]1[N:17]=[CH:16][C:15]([S:12]([N:17]([CH2:16][C:15]([OH:28])=[O:1])[CH3:18])(=[O:13])=[O:14])=[CH:20][CH:19]=1)[C:24]#[C:25][CH3:26]

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 15129470HCID 15129470, compoundHCID 86756676HCID 86756676, compound

Product 1

HCID 22645084HCID 22645084, compoundYield 45%

Procedure

To a solution of 0.77 mL (19.3 mmol) of 2- butynl-ol and 0.18 g (4.37 mmol) of sodium hydroxide were heated at 100° C. for one hour. [(6-chloro-pyridine-3-sulfonyl)methyl-amino]-acetic acid tert-butyl ester (1.0 g, 3.12 mmol) was added to this solution. Additional butynol was added to facilitate stirring, and the reaction was stirred at 100° C. overnight. The reaction was cooled, diluted with water, and washed with ethyl acetate. The aqueous layer was acidified with 2N HCl, and extracted with ethyl acetate (2×). The combined organics were washed with brine, dried over MgSO4, concentrated to solids which were slurried in 1:1:1 dichloromethane: hexane:ethyl acetate to afford 0.4 g (45%) of [(6-but-2-ynyloxy-pyridine-3-sulfonyl)-methyl-amino]-acetic acid as an off-white solid. Electrospray Mass Spec 299.0 (M+H)+

Workup

  1. stirringthe reaction was stirred at 100° C. overnight
  2. temperatureThe reaction was cooled
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to solids which

Sources & evidence

ORD record
ord-36478d1d8fff4c6c8fc8a51e0fe75ee2
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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