Water → methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate

HRID 1924379Notes

Reaction equation

[C:1]([NH:7][NH:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].O.C([O-])(O)=O.[Na+]>O=P(Cl)(Cl)Cl>[CH2:2]([C:1]1[O:10][C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[N:8][N:7]=1)[CH2:3][CH:4]=[CH2:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl N-[(2-pent-4-enoylhydrazino)carbonyl]-L-valinate (from Step 3) was heated at 80° C. for 2 h in POCl3 (0.1 M solution). The mixture was cooled at 0° C. and water was carefully added. Solid NaHCO3 was added until the mixture reached pH 7, then the mixture was extracted with EtOAc and the organic layer dried over Na2SO4 to obtain a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ: 8.42 (d, J 15.7, 1H), 5.88-5.78 (m, 1H), 5.08 (d, J 17.2, 1H), 5.01 (d, J 10.3, 1H), 4.04 (dd, J 7.1, 14.2, 1H), 3.64 (s, 3H), 2.75 (t, J 7.3, 2H), 2.39 (m, 2H), 2.13-2.06 (m, 1H), 0.94 (d, J 3.9, 3H), 0.92 (d, J 3.9, 3H). MS (ES+) C12H19N3O3 requires: 253 found: 254 (M+H+).

Workup

extractionthe mixture was extracted with EtOAc
dry with materialthe organic layer dried over Na2SO4
customto obtain a pale yellow oil

Sources & evidence

ORD record: ord-34283cb695d8482d8e4f500ead1b907c
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178520B2

Reaction notes

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