Benzyl azide → HCID 68001957, compound

HRID 536779Notes

Reaction equation

HRID 536779 reaction equation
[CH2:1]([C@@H:8]1[C@@H:12]([CH2:13][C:14]#[CH:15])[O:11][C:10]([CH3:17])([CH3:16])[O:9]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:18]([N:25]=[N+:26]=[N-:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>S([O-])([O-])(=O)=O.[Cu+2].O.C(O)(C)(C)C>[CH2:18]([N:25]1[CH:15]=[C:14]([CH2:13][C@@H:12]2[C@@H:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[O:9][C:10]([CH3:16])([CH3:17])[O:11]2)[N:27]=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 12152Benzyl azideHCID 23667548Sodium AscorbateHCID 56594809HCID 56594809, compound

Product 1

HCID 68001957HCID 68001957, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a solution of (4R,5R)-4-heptyl-2,2-dimethyl-5-(prop-2-ynyl)-1,3-dioxolane (14 mg, 0.059 mmol) in a water/t-butanol mixture (0.11, 0.11 mL), was added benzyl azide (8.5 μL, 1.1 eq), copper sulfate (56 μL of a 0.1 M sol'n, 0.1 eq), and sodium ascorbate (56 μL of a 1 M sol'n, 1 eq). The mixture was stirred at room temperature overnight to yield the title compound (21.1 mg, 97%). 1H NMR (300 MHz, CDCl3) δ 7.35 (m, 3H), 7.25 (m, 2H), 5.54 (d, 14.7 Hz, 1H), 5.45 (d, 14.7 Hz, 1H), 3.86 (m, 1H), 3.64 (m, 1H), 3.03 (dd, 4.2 Hz, 15.3 Hz, 1H), 2.92 (dd, 6.9 Hz, 15.3 Hz, 1H), 1.55-1.23 (m, 12H), 1.26 (s, 3H), 1.23 (s, 3H), 0.87 (t, 6.8 Hz, 3H). LRMS (APCI+) found 372.5, [M+H]+.

Sources & evidence

ORD record
ord-669b73a460b8408cb24bd6e564f164d6
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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