(S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

Base Information

Chemical Name:(S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate
CAS No.:1138161-39-3
Molecular Formula:C₁₄H₁₆N₂O₃S₂
Molecular Weight:324.425
Hs Code.:

Synonyms:(S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

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Chemical Property of (S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

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Technology Process of (S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

There total 2 articles about (S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)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: 76.0%

: 1138161-38-2
(S(S),R)-allyl methyl [N-(p-toluenesulfinyl)amino(thiazol-2-yl)methyl]malonate

: 1138161-39-3
(S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triethylamine; In tetrahydrofuran; for 2h; Reflux;
DOI:10.1002/anie.200804138

Reference yield:

: 1138161-37-1
(S)-(thiazol-2-ylmethilidene)-p-toluenesulfinamide

: 1138161-39-3
(S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

Guidance literature:: Multi-step reaction with 2 steps

1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; formic acid / tetrahydrofuran / Reflux

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; sodium hexamethyldisilazane; triethylamine; In tetrahydrofuran;
DOI:10.1021/acs.joc.8b00045

Reference yield:

: 1138161-39-3
(S(S),R)-methyl N-(p-toluenesulfinyl)-3-amino-3-(thiazol-2-yl)propanoate

: 1138161-44-0
N-{N-tert-butoxycarbonyl-L-valinyl-[L-(2-tert-butyldiphenylsilyloxyethyl)imino-tert-leucyl]-L-tert-leucyl-[(3S)-3-methyl-L-phenylalanyl]}-3-amino-3-(thiazol-2-yl)propanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: trifluoroacetic acid / methanol

2: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane

3: palladium on activated charcoal; hydrogen / methanol

4: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane; N,N-dimethyl-formamide

5: hydrogenchloride / water; 1,4-dioxane

6: mercuric triflate; 2,6-dimethylpyridine / acetonitrile

7: hydrazine hydrate / ethanol / 70 °C

8: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate / dichloromethane; N,N-dimethyl-formamide

With 2,6-dimethylpyridine; hydrogenchloride; palladium on activated charcoal; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; mercuric triflate; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate; In 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/acs.joc.8b00045