3-Butyn-1-OL → HCID 58124802, compound

HRID 1971738Notes

Reaction equation

[C:1]([N:5]1[CH2:33][CH2:32][CH2:31][CH2:30][C:8]2[C:9]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([N:20]=[N+:21]=[N-:22])[C:16]([O:23][CH3:24])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:34])([CH3:4])([CH3:3])[CH3:2].[CH2:35]([OH:39])[CH2:36][C:37]#[CH:38].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].C(C(N(C(C1N=NNC=1)CC1C=CC=CC=1)C(C1N=NNC=1)CC1C=CC=CC=1)C1N=NNC=1)C1C=CC=CC=1>O.[O-]S([O-])(=O)=O.[Cu+2].C(O)C>[C:1]([N:5]1[CH2:33][CH2:32][CH2:31][CH2:30][C:8]2[C:9]([C:25]3[S:26][CH:27]=[CH:28][CH:29]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([N:20]5[CH:38]=[C:37]([CH2:36][CH2:35][OH:39])[N:22]=[N:21]5)[C:16]([O:23][CH3:24])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:34])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

In a microwave tube were mixed 52 mg of azide 20c, 10 ul of 3-butyn-1-ol, 2 ml of water, 2 ml of ethanol, 3.5 mg of CuSO4, 11 mg of sodium ascorbate and 11 mg of tris(benzyltriazolylmethyl)amine. The mixture was heated at 100° C. for 30 min., and then cooled and diluted with water. The product was extracted into ethyl acetate. The organic layer was washed, dried and concentrated, and the residue was purified by silicagel chromatography (using a gradient of heptane/ethyl acetate as eluent), and provided 29 mg of product 20d. LCMS-ESI: [M+1] 564.2.

Workup

temperaturecooled
extractionThe product was extracted into ethyl acetate
washThe organic layer was washed
customdried
concentrationconcentrated
customthe residue was purified by silicagel chromatography (

Sources & evidence

ORD record: ord-3bd7cba84e15423db9a03ee03c67e893
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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