HCID 89459987, compound → HCID 89459986, compound

HRID 1776608Notes

Reaction equation

HRID 1776608 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])[S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][CH:4]=1>Cl.O1CCOCC1.O>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:14][C:15]([OH:17])=[O:16])[S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][CH:4]=1

Participants

5

Reactant 1

HCID 89459987HCID 89459987, compound

Product 1

HCID 89459986HCID 89459986, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl 2-(N-(4-(methylthio)phenyl)methylsulfonamido)acetate (220 mg, 0.664 mmol) was dissolved in HCl 4M in Dioxane (4 ml). The reaction was stirred at RT for 8 hours. The reaction mixture was diluted with water and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated under vacuum, and the crude product was triturated with Petroleum Ether to give 2-(N-(4-(methylthio)phenyl)methyl-sulfonamido)acetic acid (150 mg, 82% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customthe crude product was triturated with Petroleum Ether

Sources & evidence

ORD record
ord-2c0ae55da6b6416a9b6904a9f50d3405
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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