N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Base Information

Chemical Name:N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine
CAS No.:864665-80-5
Molecular Formula:C₂₅H₃₂N₂O₇
Molecular Weight:472.538
Hs Code.:

Synonyms:N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

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Chemical Property of N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

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Technology Process of N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

There total 4 articles about N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine 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: 60.0%

: 864665-79-2
N-[2-amino-4-benzyloxy-5-methoxybenzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

: 24424-99-5
di-tert-butyl dicarbonate

: 864665-80-5
N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Guidance literature:: In tetrahydrofuran; Heating / reflux;

Reference yield:

: 60547-92-4
4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid

: 864665-80-5
N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 16 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 16 h / -20 - 20 °C / Inert atmosphere

3: lithium borohydride / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

4: tin(II) chloride dihdyrate; methanol / 3 h / Reflux

5: tin(II) chloride dihdyrate; methanol / tetrahydrofuran / 16 h / Reflux

With methanol; lithium borohydride; oxalyl dichloride; tin(II) chloride dihdyrate; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/acs.jmedchem.7b00736

Reference yield:

: 64154-78-5
4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride

: 864665-80-5
N-[4-benzyloxy-5-methoxy-2-(tert-butyloxycarbonylamino)benzoyl]-(2S,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 16 h / -20 - 20 °C / Inert atmosphere

2: lithium borohydride / tetrahydrofuran / 4.5 h / 0 - 20 °C / Inert atmosphere

3: tin(II) chloride dihdyrate; methanol / 3 h / Reflux

4: tin(II) chloride dihdyrate; methanol / tetrahydrofuran / 16 h / Reflux

With methanol; lithium borohydride; tin(II) chloride dihdyrate; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/acs.jmedchem.7b00736