Hydrochloric Acid → HCID 178472763, compound

HRID 1423929Notes

Reaction equation

HRID 1423929 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:13])=[CH:7][C:8](=[O:12])[S:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:21]([O:23][C:24](=[O:29])[CH2:25][N:26]=[C:27]=[O:28])[CH3:22].Cl>ClCCl>[CH2:21]([O:23][C:24](=[O:29])[CH2:25][NH:26][C:27]([C:7]1[C:8](=[O:12])[S:9][C:10]2[C:5]([C:6]=1[OH:13])=[CH:4][CH:3]=[C:2]([F:1])[CH:11]=2)=[O:28])[CH3:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 178516555HCID 178516555, compound

Product 1

HCID 178472763HCID 178472763, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Fluoro-4-hydroxy-thiochromen-2-one (2.0 g, 10.2 mmol) was dissolved in a mixture of triethylamine (1.7 mL, 12.23 mmol) and dichloromethane (50 mL). Isocyanato-acetic acid ethyl ester (1.4 mL, 12.23 mmol) was added to the solution and the reaction stirred overnight (18 h) at ambient temperature. The reaction mixture was acidified to pH 3 using 1N HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, and the crude residue purified by silica gel chromatography (10%-40% ethyl acetate in hexanes) to provide [(7-fluoro-4-hydroxy-2-oxo-2H-thiochromene-3-carbonyl)-amino]-acetic acid ethyl ester (900 mg, 30%). MS ESI(−) m/e: 324.117 (M−1).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe crude residue purified by silica gel chromatography (10%-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-524677c632ea400291a22e0e01752024
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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