Hydrazine → tert-butyl N-[(1R)-1-(1,3,4-oxadiazol-2-yl)propyl]carbamate

HRID 476127Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1N=CN(C([N:22]2[CH:26]=NC=C2)=O)C=1.[NH2:27]N.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)Br>C(Cl)Cl>[O:11]1[CH:26]=[N:22][N:27]=[C:10]1[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:13][CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

(2R)-2-(tert-butoxycarbonylamino)butanoic acid (5 g, 24.60 mmol) was dissolved in DCM (500 mL) and cooled to 0° C. CDI (4.188 g, 25.83 mmol) was added and the reaction stirred for 60 minutes. Formic hydrazine (1.477 g, 24.60 mmol) was added and the reaction stirred at 0° C. for 45 minutes then allowed to reach ambient temperature overnight. The reaction was cooled to 0° C. and treated with PS-PPh3 (22.88 g, 49.20 mmol) and CBr4 (16.32 g, 49.20 mmol) The reaction was allowed to warm slowly to ambient temperature over 2 hours, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (25 to 50% EtOAc/Petrol) to give the sub-title compound as a colourless oil (2.30 g, 41%); 1H NMR (400.0 MHz, DMSO) d 0.88 (t, 3H), 1.27-1.39 (2×s, 9H), 1.75-1.87 (m, 2H), 4.71 (dd, 1H), 7.62 (d, 1H), 9.17 (s, 1H) MS ES(+) 228.

Workup

stirringthe reaction stirred at 0° C. for 45 minutes
waitto reach ambient temperature overnight
temperatureThe reaction was cooled to 0° C.
temperatureto warm slowly to ambient temperature over 2 hours
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (25 to 50% EtOAc/Petrol)

Sources & evidence

ORD record: ord-41c0343008404f06b8cfbf76fb9b57ab
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637666B2

Reaction notes

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