Methanol → 2-((5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)thio)-5-thiazolecarboxylic acid

HRID 1379797Notes

Reaction equation

[CH3:1][C:2]1[C:3]([S:16][C:17]2[S:18][C:19]([C:22]([O:24]CC)=[O:23])=[CH:20][N:21]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.[Li+].[OH-].CO>C1COCC1>[CH3:1][C:2]1[C:3]([S:16][C:17]2[S:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][N:21]=2)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:12])([CH3:13])[C:10]=2[CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 0.183 g (0.47 mmol) of ethyl 2-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthylthio)-5-thiazolecarboxylate (Compound 14) in 2.0 mL of THF was added 1.0 mL of LiOH (2.1N aqueous solution) and 1.0 mL of MeOH. The solution was heated at 50° C. for 1 h, cooled to room temperature and concentrated in vacuo. The residue was diluted with water, the aqueous layer acidified to pH=1 using 10% HCl and extracted with ether. The combined organic layers were washed with brine, dried (MgSO4), filtered, and the solvents removed in vacuo to give the title compound as a white solid (131 mg, 78%): PNMR (300 MHz, CD3OD) δ 1.28 (s, 6H), 1.32 (s, 6H), 1.73 (s, 4H), 2.40 (s, 3H), 7.42 (s, 1H), 7.63 (s, 1H), 8.12 (s, 1H).

Workup

temperaturecooled to room temperature
concentrationconcentrated in vacuo
additionThe residue was diluted with water
extractionextracted with ether
washThe combined organic layers were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
customthe solvents removed in vacuo

Sources & evidence

ORD record: ord-e92edfc4b2344efe9b6d2b9fef51181e
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05672710

Reaction notes

Loading…