(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

Base Information

Chemical Name:(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester
CAS No.:873841-02-2
Molecular Formula:C₂₈H₃₂Cl₂N₂O₆
Molecular Weight:563.478
Hs Code.:

Synonyms:(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

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Chemical Property of (2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

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Technology Process of (2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

There total 9 articles about (2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester 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: 63.0%

: 873841-01-1
(2S,2'R)-N-[N-(tert-butoxycarbonyl)-2-(hydroxymethyl)prolin-1-yl]-O-(2,6-dichlorobenzyl)tyrosyne methyl ester

: 873841-02-2
(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; for 5h;
DOI:10.1021/jo0517287

Reference yield:

: 873840-92-7
(R)-1-tert-butyl 2-methyl 2-vinylpyrrolidine-1,2-dicarboxylate

: 873841-02-2
(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaOH / H₂O; methanol / 1 h / 50 °C

2.1: 92 percent / HATU; ethyldiisopropylamine / 1-methyl-pyrrolidin-2-one / 0.42 h

3.1: ozone / CH₂Cl₂ / -78 °C

3.2: 77 percent / Na[BH(OAc)3] / CH₂Cl₂ / 24 h / -78 - 20 °C

4.1: 63 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 5 h

With sodium hydroxide; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylazodicarboxylate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; toluene; 4.1: Mitsunobu reaction;
DOI:10.1021/jo0517287

Reference yield:

: 873840-88-1
(2R,3R)-4-oxo-2-(trichloromethyl)-1-aza-3-oxabicyclo[3.3.0]octane-5-carbaldehyde

: 873841-02-2
(2S,4'R)3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-[5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]oct-2-yl]propionic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium tert-butoxide / toluene / 2 h / 80 °C

1.2: 74 percent / toluene / 1 h / 20 °C

2.1: acetyl chloride / 168 h / 20 °C

3.1: 73 percent / ethyldiisopropylamine / CH₂Cl₂ / 60 h / 20 °C

4.1: NaOH / H₂O; methanol / 1 h / 50 °C

5.1: 92 percent / HATU; ethyldiisopropylamine / 1-methyl-pyrrolidin-2-one / 0.42 h

6.1: ozone / CH₂Cl₂ / -78 °C

6.2: 77 percent / Na[BH(OAc)3] / CH₂Cl₂ / 24 h / -78 - 20 °C

7.1: 63 percent / triphenylphosphine; DEAD / tetrahydrofuran; toluene / 5 h

With sodium hydroxide; potassium tert-butylate; ozone; N-ethyl-N,N-diisopropylamine; acetyl chloride; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylazodicarboxylate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; water; toluene; 1.2: Wittig olefination / 7.1: Mitsunobu reaction;
DOI:10.1021/jo0517287