tert-Butyl 2-bromo-2-methylpropionate → {2-[(2-Tert-butoxy-1,1-dimethyl-2-oxoethyl)thio]-4-methyl-1,3-thiazol-5-yl}acetic acid

HRID 914288Notes

Reaction equation

[SH:1][C:2]1[S:3][C:4]([CH2:8][C:9]([OH:11])=[O:10])=[C:5]([CH3:7])[N:6]=1.[C:12]([O:16][C:17](=[O:22])[C:18](Br)([CH3:20])[CH3:19])([CH3:15])([CH3:14])[CH3:13]>CO.[OH-].[Na+]>[C:12]([O:16][C:17](=[O:22])[C:18]([S:1][C:2]1[S:3][C:4]([CH2:8][C:9]([OH:11])=[O:10])=[C:5]([CH3:7])[N:6]=1)([CH3:20])[CH3:19])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 60 °C

Procedure

Commercially available (2-mercapto-4-methyl-1,3-thiazol-5-yl)acetic acid (15 g) was dissolved in methanol (360 mL) and 1N aqueous sodium hydroxide solution (174 mL), 2-bromo-2-methylpropionic acid tert-butyl ester (19.4 g) was added, and the mixture was stirred at 60° C. for 6 hr. The reaction mixture was concentrated, the residue was dissolved in water, and the mixture was acidified with 10% aqueous citric acid solution. The precipitated solid was collected by filtration, and dried under reduced pressure to give the title compound (25 g) as a white solid.

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in water
filtrationThe precipitated solid was collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-ce977d1b08984a659149cd06b1f7bfe4
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026370B2

Reaction notes

Loading…