HCID 58158056, compound → HCID 59287157, compound

HRID 1255509Notes

Reaction equation

[CH:1]1([C@H:6]([N:11]=[C:12]=[O:13])[C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([C@@H:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[OH:24])[CH2:15][CH2:16][CH:17]=[CH2:18]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C.CCOC(C)=O.Cl>[CH:1]1([C@H:6]([NH:11][C:12]([O:24][C@@H:20]2[CH2:21][CH2:22][CH2:23][C@H:19]2[CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])=[O:13])[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of methyl (2S)-cyclopentyl(isocyanato)acetate (1.57 g, 8.56 mmol) and (1R,2R)-2-pent-4-en-1-ylcyclopentanol (Intermediate A9) (1.20 g, 7.78 mmol) in PhMe (56 mL) was treated portionwise with DMAP (0.95 g, 7.78 mmol). The resulting mixture was stirred for 5 hours at 85° C., then cooled to 20° C., and diluted with EtOAc and HCl(aq.) (1N). The organic layer was separated, washed with brine, and dried over Na2SO4. Filtration and removal of the volatiles gave a residue that was purified by column chromatography (gradient elution, 4-40% Et2O/petroleum ether) to afford the title compound (1.97 g, 76%) as an oil. LCMS (ES+) m/z, 338 (M+H)+.

Workup

temperaturecooled to 20° C.
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
filtrationFiltration and removal of the volatiles
customgave a residue that
customwas purified by column chromatography (gradient elution, 4-40% Et2O/petroleum ether)

Sources & evidence

ORD record: ord-ad8435bd51e548a8b6e41d026845bd9b
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461107B2

Reaction notes

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