Azidobenzene → methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate

HRID 1422649Notes

Reaction equation

HRID 1422649 reaction equation
[OH:1][C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH2:15][C:16]([CH3:18])=[CH2:17])[CH2:3][CH2:4][N:5]([C:10]([CH3:14])([C:12]#[CH:13])[CH3:11])[C:6](=[O:9])[O:7][CH3:8].[N:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[N+:26]=[N-:27].O=C1O[C@H]([C@H](CO)O)C(O)=C1O>O.CC(O)(C)C.[O-]S([O-])(=O)=O.[Cu+2].O>[OH:1][C:2]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH2:15][C:16]([CH3:18])=[CH2:17])[CH2:3][CH2:4][N:5]([C:10]([C:12]1[N:27]=[N:26][N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:13]=1)([CH3:14])[CH3:11])[C:6](=[O:9])[O:7][CH3:8]

Participants

7

Reactant 3

HCID 69319Azidobenzene2×HCID 54670067L-Ascorbic Acid2×HCID 86669141Methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-methylbut-3-yn-2-yl)carbamate

Product 1

HCID 68160533methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamateYield 44%

Reagents, catalysts & solvents 3

HCID 61499Cupric sulfate monohydrateCatalystHCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred solution of methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-methylbut-3-yn-2-yl)carbamate (26 mg, 0.081 mmol) and azidobenzene (29 mg, 0.24 mmol) in H2O (1 mL) and t-BuOH (1 mL) was added ascorbic acid (3.2 mg, 0.016 mmol)followed by CuSO4.H2O (0.5 mg, 0.002 mmol). The mixture was stirred at rt for 2 d. Additional azidobenzene (29 mg, 0.24 mmol), ascorbic acid (3.2 mg, 0.016 mmol) and CuSO4.5H2O (0.5 mg, 0.002 mmol) were added. The mixture was stirred for 4 h at rt and purified by prep HPLC to afford methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate (16 mg, 44%) as an oil. LC-MS Method 1 tR=2.00 min, m/z=449.

Workup

  1. stirringThe mixture was stirred for 4 h at rt
  2. custompurified by prep HPLC

Sources & evidence

ORD record
ord-2580663f58f942fc8c87fbae5997cec2
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

Loading…