Nitrogen → 2(S)-Boc-amino-1-(5-pyridin-3-yl-[1,3,4]oxadiazol-2-yl)-butan-1-ol

HRID 1444583

Reaction equation

[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1.[Li]CCCC.[N:17]#N.CCOCC.[C:24]([C@:31](N)([CH2:34][CH3:35])[CH:32]=[O:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[C:24]([C@@H:31]([CH2:34][CH3:35])[C:32]([NH2:17])([C:5]1[O:1][C:2]([C:6]2[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=2)=[N:3][N:4]=1)[OH:33])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

Conditions

Temperature: -45 °C

Procedure

To a stirred solution of the 3-[1.3.4]oxadiazol-2-yl-pyridine (5 g, 34 mmol) in THF (100 mL) was added HMPA (5 mL) and n-BuLi (1.6 M solution in hexane, 21.25 mL) drop wise under N2 at −78° C. After 1 h, MgBr.Et2O (8.77 g, 34 mmol) was added and the reaction mixture was allowed to warm to −45° C. for 1 h before being treated with 2(S)-Boc-aminobutyraldehyde (4.22 g, 22.1 mmol) in THF (20 mL). The reaction mixture was stirred for 1 h, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 2(S)-Boc-amino-1-(5-pyridin-3-yl-[1.3.4]oxadiazol-2-yl)-butan-1-ol (1.5 g).

Workup

customquenched with saturated NH4Cl
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried with MgSO4
concentrationconcentrated
customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record: ord-e4f272ee0a854bb688e46ecc184c969f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662849B2

Linked notes

Loading…