[1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

Base Information

Chemical Name:[1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide
CAS No.:331821-77-3
Molecular Formula:C₂₁H₃₂N₂O₅
Molecular Weight:392.495
Hs Code.:

Synonyms:[1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

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Chemical Property of [1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

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Technology Process of [1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

There total 11 articles about [1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide 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:

: 536-74-3
phenylacetylene

: 331821-77-3
[1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-BuLi; 18-crown-6 / tetrahydrofuran; hexane / 1.17 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C

2.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

3.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

4.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

5.1: Cu(TBS)2 / toluene / Heating

6.1: conc. HCl; triethylsilane / tetrahydrofuran / 6 h / 70 °C

7.1: 720 mg / Et₃N / acetonitrile / 20 °C

8.1: 74 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

9.1: CuBr*DMS / diethyl ether / 0 °C

9.2: 90 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

10.1: 66 percent / AlMe₃ / CH₂Cl₂; toluene / 12 h / 20 °C

With hydrogenchloride; triethylsilane; n-butyllithium; copper(I) bromide dimethylsulfide complex; 18-crown-6 ether; hydrogen; trimethylaluminum; N,N-dimethyl-aniline; ethylenediamine; triethylamine; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 8.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i

Reference yield:

: 241478-33-1
tert-butyl (4S)-4-<(1R)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 331821-77-3
[1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

Guidance literature:: Multi-step reaction with 9 steps

1.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

2.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

4.1: Cu(TBS)2 / toluene / Heating

5.1: conc. HCl; triethylsilane / tetrahydrofuran / 6 h / 70 °C

6.1: 720 mg / Et₃N / acetonitrile / 20 °C

7.1: 74 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

8.1: CuBr*DMS / diethyl ether / 0 °C

8.2: 90 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

9.1: 66 percent / AlMe₃ / CH₂Cl₂; toluene / 12 h / 20 °C

With hydrogenchloride; triethylsilane; copper(I) bromide dimethylsulfide complex; hydrogen; trimethylaluminum; N,N-dimethyl-aniline; ethylenediamine; triethylamine; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; acetonitrile; 7.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i

Reference yield:

: 331821-71-7
cis-[4S,4(1'R)]-4-(1'-hydroxy-3'-phenyl-2'-propenyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 331821-77-3
[1R,2R,3S,2(1'R,2'S)]-2-[1'-hydroxy-2'-(tert-butoxycarbonylamino)butyl]-3-phenylcyclopropane-1-carboxylic acid N-methoxy-N-methylamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

2.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

3.1: Cu(TBS)2 / toluene / Heating

4.1: conc. HCl; triethylsilane / tetrahydrofuran / 6 h / 70 °C

5.1: 720 mg / Et₃N / acetonitrile / 20 °C

6.1: 74 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

7.1: CuBr*DMS / diethyl ether / 0 °C

7.2: 90 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

8.1: 66 percent / AlMe₃ / CH₂Cl₂; toluene / 12 h / 20 °C

With hydrogenchloride; triethylsilane; copper(I) bromide dimethylsulfide complex; trimethylaluminum; N,N-dimethyl-aniline; triethylamine; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 6.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i