Sodium Azide → (3S,5S)-5-[(S)-1-Azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one

HRID 1694885Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][CH2:13][C@H:14]([C@H:16]1[O:20][C:19](=[O:21])[C@H:18]([CH:22]([CH3:24])[CH3:23])[CH2:17]1)Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN1C(=O)N(C)CCC1>[N:1]([C@H:14]([C@H:16]1[O:20][C:19](=[O:21])[C@H:18]([CH:22]([CH3:24])[CH3:23])[CH2:17]1)[CH2:13][O:12][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 40 °C

Procedure

5.10 g of sodium azide (78.5 mmol) was added to a solution of 22.33 g of (3S,5S)-5-[(1R)-2-benzyloxy-1-bromoethyl]-3-isopropyldihydrofuran-2-one obtained in Example (1d) (65.4 mmol) in N,N′-dimethylpropyleneurea (130 ml) at room temperature, and the mixture was stirred at 40° C. for three days. The reaction mixture was cooled and then poured into ice water, followed by extraction with diethyl ether. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1) to obtain 10.19 g of the title compound (yield: 51%).

Workup

temperatureThe reaction mixture was cooled
extractionfollowed by extraction with diethyl ether
washThen, the organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter filtration
customthe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent:n-hexane/ethyl acetate=6/1)

Sources & evidence

ORD record: ord-94aca53dc13a447c857faf9c558ba6ed
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158790B2

Reaction notes

Loading…