Sodium ethoxide → 2-Ethoxy-N-[4-(2-furyl)-5-(tetrahydropyran-4-ylcarbonyl)thiazol-2-yl]acetamide

HRID 1361862Notes

Reaction equation

[O-:1][CH2:2][CH3:3].[Na+].Br[CH2:6][C:7]([NH:9][C:10]1[S:11][C:12]([C:20]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:21])=[C:13]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)=[O:8]>C(O)C>[CH2:2]([O:1][CH2:6][C:7]([NH:9][C:10]1[S:11][C:12]([C:20]([CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)=[O:21])=[C:13]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)=[O:8])[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium ethoxide (62.0 mg, 0.900 mmol) was dissolved in ethanol (2 mL), and Compound 531 (120 mg, 0.300 mmol) was added thereto, followed by stirring at 60° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1) and crystallized from 2-propanol to afford the entitled Compound 532 (53.4 mg, 49%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=99:1)
customcrystallized from 2-propanol

Sources & evidence

ORD record: ord-ab2de8eeb0694048b4fb2840ddba0cee
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880013B2

Reaction notes

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