Ethyl bromopyruvate → HCID 58654501, compound

HRID 1170545Notes

Reaction equation

Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[N:10]1([C:15]2[N:20]=[C:19]([CH:21]3[CH:25]([C:26](=[S:28])[NH2:27])[CH2:24][CH2:23][N:22]3[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:18]=[C:17]([CH3:36])[N:16]=2)[CH:14]=[CH:13][N:12]=[CH:11]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:7]([O:6][C:4]([C:3]1[N:27]=[C:26]([CH:25]2[CH2:24][CH2:23][N:22]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:21]2[C:19]2[CH:18]=[C:17]([CH3:36])[N:16]=[C:15]([N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)[N:20]=2)[S:28][CH:2]=1)=[O:5])[CH3:8]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 3-bromo-2-oxopropanoate (350 mg, 1.79 mmol) was added to a solution of tert-butyl 2-(2-(1 H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-carbamothioylpyrrolidine-1-carboxylate (700 mg, 1.80 mmol) in DCM (20 mL) at rt under an atmosphere of N2. The reaction mixture was heated to 100° C. for 2 h then cooled to rt. Sodium bicarbonate (20 mL, sat. aq.) was added and the mixture extracted with DCM (2×20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was then purified using column chromatography (DCM to 9:1 DCM/MeOH) to afford 500 mg (80%) of 2-[1-tert-butoxycarbonyl-2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-3-yl]-thiazole-4-carboxylic acid ethyl ester as a yellow oil.

Workup

temperaturethen cooled to rt
extractionthe mixture extracted with DCM (2×20 mL)
dry with materialThe combined organic layers were dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was then purified

Sources & evidence

ORD record: ord-a7d25b3eae3c42da8e612877cc7fbf71
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825256B2

Reaction notes

Loading…