(S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

Base Information

Chemical Name:(S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate
CAS No.:1613625-26-5
Molecular Formula:C₃₁H₃₄N₂O₆
Molecular Weight:530.621
Hs Code.:

Synonyms:(S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

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Chemical Property of (S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

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Technology Process of (S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

There total 19 articles about (S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate 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: 78.0%

: 1613625-25-4
(S)-methyl 2-(tert-butoxycarbonylamino)-3-[4-(trifluoromethylsulfonyloxy)naphthalen-1-yl]propanoate

: 149965-78-6
N-benzyloxycarbonyl-but-3-ynyl-1-amine

: 1613625-26-5
(S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

Guidance literature:: With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-tert-butyl phosphine; triethylamine; In hexane; acetonitrile; for 16h; Inert atmosphere; Reflux;

Reference yield:

: (S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-hydroxynaphthalen-1-yl)propanoate

: 1613625-26-5
(S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 2 h / 0 - 20 °C

2: tri-tert-butyl phosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / acetonitrile; hexane / 16 h / Inert atmosphere; Reflux

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-tert-butyl phosphine; triethylamine; In hexane; acetonitrile;

Reference yield:

: 15971-29-6
4-methoxy-1-naphthaldehyde

: 1613625-26-5
(S)-methyl 3-{4-[4-(benzyloxycarbonylamino)but-1-ynyl]naphthalen-1-yl}-2-(tert-butoxycarbonylamino)propanoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 0 °C

1.2: 36 h / 20 °C

2.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h / 20 °C / 760.05 Torr

3.1: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 20 °C

4.1: n-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C

4.2: 1.8 h / -78 - 20 °C

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C

5.2: 0.08 h / -78 °C

5.3: 16 h / -78 - 24 °C

6.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.2 h / 0 - 20 °C

7.1: hydrogen; palladium 10% on activated carbon / water / 3 h / 20 °C / 760.05 Torr

8.1: acetic acid; hydrogen bromide / 3 h / Reflux

9.1: acetyl chloride / 4 h / 0 °C / Reflux

10.1: sodium hydrogencarbonate / methanol; water / 1 h / 0 - 20 °C

11.1: pyridine / 2 h / 0 - 20 °C

12.1: tri-tert-butyl phosphine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / acetonitrile; hexane / 16 h / Inert atmosphere; Reflux

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tri-tert-butyl phosphine; palladium 10% on activated carbon; water; hydrogen bromide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydrogencarbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; sodium hydroxide; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; cyclohexane; water; acetonitrile;