Chloride → HCID 86622744, compound

HRID 1020240Notes

Reaction equation

HRID 1020240 reaction equation
[Cl-].[C:2]([O:6][C:7](=[O:16])[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14]Cl)[N:13]=1)([CH3:5])([CH3:4])[CH3:3].C(=O)([O-])[O-].[K+].[K+].[CH3:23][O:24][CH2:25][CH2:26][OH:27]>>[C:2]([O:6][C:7](=[O:16])[NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][O:27][CH2:26][CH2:25][O:24][CH3:23])[N:13]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 4

HCID 312ChlorideHCID 80192-MethoxyethanolHCID 11430Potassium CarbonateHCID 45117840tert-Butyl (4-(chloromethyl)thiazol-2-yl)carbamate

Product 1

HCID 86622744HCID 86622744, compoundYield 46%

Conditions

Temperature
90 °C

Procedure

A mixture of the chloride (Intermediate II, 420 mg, 1.69 mmol) and potassium carbonate (818 mg, 5.92 mmol) in 2-methoxyethanol (12 ml) was stirred for 2 hours at 90° C. TLC indicated complete conversion. The mixture was filtered through a pad of celite and the solvent was removed under vacuum. The residue was purified by column chromatography (silica gel, ethyl acetate/heptane, 25-70% gradient) to give 46% (225 mg, 781 μmol) of title compound as pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 1.56 (s, 9H), 3.39 (s, 3H), 3.54-3.58 (m, 2H), 3.64-3.69 (m, 2H), 4.58 (s, 2H), 6.82 (s, 1H).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe solvent was removed under vacuum
  3. customThe residue was purified by column chromatography (silica gel, ethyl acetate/heptane, 25-70% gradient)

Sources & evidence

ORD record
ord-b7a386d64a61453781a4ef0ab09394e0
Source dataset
uspto-grants-2014_05
Patent number
US08716320B2

Reaction notes

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