(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

Base Information

Chemical Name:(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide
CAS No.:745794-09-6
Molecular Formula:C₁₉H₂₈N₂O₅
Molecular Weight:364.442
Hs Code.:

Synonyms:(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

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Chemical Property of (Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

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Technology Process of (Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

There total 2 articles about (Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 51307-59-6
N-(4-methoxybenzyl)hydroxylamine

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 745794-09-6
(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

Guidance literature:: With magnesium sulfate; In dichloromethane; at 20 ℃;
DOI:10.1021/jo0496547

Reference yield:

: 108149-63-9
4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 745794-09-6
(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

Guidance literature:: Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 8.1 g / MgSO₄ / CH₂Cl₂ / 20 °C

With oxalyl dichloride; magnesium sulfate; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation;
DOI:10.1021/jo0496547

Reference yield:

: 745794-09-6
(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-ylidene]-4-methoxybenzylamine N-oxide

: (1R,5S)-{5-[benzyloxycarbonyl-(4-methoxybenzyl)amino]-2,3-dihydroxycyclopentyl}carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 87 percent / ZnBr₂ / tetrahydrofuran; diethyl ether / 4 h / -70 °C

2: Zn; Cu(OAc)2; AcOH / H₂O / 2 h / 70 °C

3: NaHCO₃ / H₂O; ethyl acetate / 20 °C

4: 8.64 g / p-TsOH*H₂O / methanol / 1 h / Heating

5: (COCl)2; DMSO; Et₃N / CH₂Cl₂

6: 93 percent / tetrahydrofuran / 20 °C

7: [Ru(PCy₃)2(=CHPh)Cl₂] / CH₂Cl₂ / 24 h / 35 °C

8: 78 percent / NaHCO₃; 3-chloroperbenzoic acid / CH₂Cl₂ / 24 h / 15 °C

9: H₂SO₄ / H₂O; dioxane / 10 °C

With copper diacetate; oxalyl dichloride; sulfuric acid; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc dibromide; zinc; Grubbs catalyst first generation; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 5: Swern oxidation / 7: ring-closing metathesis;
DOI:10.1021/jo0496547