Nitrogen → 4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-(2-methoxypropan-2-yl)oxazole

HRID 82821Notes

Reaction equation

N#N.[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17]([OH:20])([CH3:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH3:21]I>C(Cl)Cl>[Si:3]([O:10][CH2:11][C:12]1[N:13]=[C:14]([C:17]([O:20][CH3:21])([CH3:19])[CH3:18])[O:15][CH:16]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 40 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(4-(((tert-butyldimethylsilyl)oxy)methyl)oxazol-2-yl)propan-2-ol (153 mg, 0.56 mmol) in CH2Cl2 (0.4 mL) was treated with MeI (0.08 mL, 1.35 mmol) followed by Ag2O (196 mg, 0.85 mmol). The resulting mixture (protected form light) was stirred overnight at 40° C. The reaction mixture was filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (7:3 hept-EA) gave the title compound as an orange oil. TLC: rf (7:3 hept-EA)=0.40. LC-MS-conditions 07: tR=0.99 min, [M+H]+=286.20.

Workup

filtrationThe reaction mixture was filtered
customthe solvent was removed under reduced pressure
customPurification of the residue by FC (7:3 hept-EA)

Sources & evidence

ORD record: ord-63f0668deede40afaa680b78eb078207
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846733B2

Reaction notes

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