2-Methyl-2-butene → 5-(2-Acetamido-4-methylthiazol-5-yl)furan-2-carboxylic acid

HRID 2386176Notes

Reaction equation

[CH:1]([C:3]1[O:7][C:6]([C:8]2[S:12][C:11]([NH:13][C:14](=[O:16])[CH3:15])=[N:10][C:9]=2[CH3:17])=[CH:5][CH:4]=1)=[O:2].P([O-])([O-])([O-])=[O:19].[Na+].[Na+].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.C1COCC1.O>[C:14]([NH:13][C:11]1[S:12][C:8]([C:6]2[O:7][C:3]([C:1]([OH:19])=[O:2])=[CH:4][CH:5]=2)=[C:9]([CH3:17])[N:10]=1)(=[O:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1.2 g of N-(5-(5-formylfuran-2-yl)-4-methylthiazol-2-yl)acetamide in 100 mL of tert-butanol was added 5 mL of water and 20 mL of 2N monobasic sodium phosphate. The resulting suspension was cooled to 0° C. while being stirred. To the chilled suspension was added 20 mL of a 2M solution of 2-methyl-2-butene in THF followed by 3 g of sodium chlorite in 10 mL of water. The reaction was allowed to warm to room temperature overnight and the upper organic layer was separated and dried over sodium sulfate and used as is in the subsequent reactions. LC/MS: 267.04 (M+H)/2.04 min.

Workup

temperatureto warm to room temperature overnight
customthe upper organic layer was separated
dry with materialdried over sodium sulfate
custom2.04 min.

Sources & evidence

ORD record: ord-6710a48b72e7496ab71fcbd1057c37c5
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268818B2

Reaction notes

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