tert-Butanol → HCID 118022810, compound

HRID 518582Notes

Reaction equation

HRID 518582 reaction equation
[C:1]1(C(O)=O)[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[CH:3][N:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.CC[O:39]C(C)=O.[CH3:43][C:44]([OH:47])([CH3:46])[CH3:45]>>[C:1]1([NH:32][C:35](=[O:39])[O:47][C:44]([CH3:46])([CH3:45])[CH3:43])[C:6]2[CH2:7][CH2:8][CH2:9][C:5]=2[CH:4]=[CH:3][N:2]=1

Participants

6

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 83669226HCID 83669226, compound

Product 1

HCID 118022810HCID 118022810, compoundYield 40%

Procedure

The title compound of step 2 (1.0 g, 6.1 mmol), diphenylphosphoryl azide (2.64 mL 12.2 mmol), and triethylamine (1.64 mL, 12.2 mmol) in tBuOH (50 mL) under N2 were heated at 80° C. for 2 h. Silica gel chromatography (PE/EtOAc=5:1) gave the title compound (570 mg, 40%) as a white solid. 1H NMR (CDCl3, 300 MHz): δ 8.18 (d, J=4.8 Hz, 1H), 7.04 (d, J=4.8 Hz, 1H), 2.90-2.97 (m, 4H), 2.06-2.12 (m, 2H), 1.49 (s, 9H). LCMS: 235 (M+1)+

Sources & evidence

ORD record
ord-de7f3de37fae421c800b163c35da36f1
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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