(R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

Base Information

• Chemical Name: (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid
• CAS No.: 1315334-27-0
• Molecular Formula: C₂₁H₂₅N₃O₄S₂
• Molecular Weight: 447.579

Synonyms:(R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

Chemical Property of (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

Chemical Property:

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Technology Process of (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid

There total 9 articles about (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid 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: 99.0%

(R)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate (1315334-26-9) + (2R)-2-methyl-L-cysteine hydrochloride → (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1315334-27-0)

Guidance literature:

With sodium hydrogencarbonate; In methanol; at 70 ℃; for 2h; aq. phosphate buffer; Inert atmosphere;

DOI:10.1021/jo201675r

Reference yield:

(R)-tert-butyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate (129095-62-1,35150-06-2) → (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1315334-27-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Lawessons reagent / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: calcium carbonate / ethanol / 20 °C / Inert atmosphere

3.1: lithium hydroxide / tetrahydrofuran; water / 0 - 20 °C

3.2: pH 1

4.1: ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / 1,4-dioxane; dichloromethane / 0 °C / Inert atmosphere

5.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 °C / Inert atmosphere

6.1: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / Inert atmosphere; aq. phosphate buffer

With Lawessons reagent; ammonia; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; calcium carbonate; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 2.1: Hantzsch cyclization;

DOI:10.1016/j.bmc.2011.02.024

Reference yield:

(R)-tert-butyl 1-(4-carbamoylthiazol-2-yl)-2-phenylethylcarbamate (1315334-25-8) → (R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxylic acid (1315334-27-0)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0 °C / Inert atmosphere

2: sodium hydrogencarbonate / methanol / 2 h / 70 °C / pH 6 / Inert atmosphere; aq. phosphate buffer

With sodium hydrogencarbonate; triethylamine; trifluoroacetic anhydride; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2011.02.024

upstream raw materials:

(R)-tert-butyl 1-(4-carbamoylthiazol-2-yl)-2-phenylethylcarbamate

(R)-tert-butyl 1-(4-cyanothiazol-2-yl)-2-phenylethylcarbamate

(R)-methyl 2-(1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazole-4-carboxylate

(R)-tert-butyl (1-amino-1-oxo-3-phenylpropan-2-yl)carbamate

Downstream raw materials:

(S,E)-2-(trimethylsilyl)ethyl 3-((S)-2-((R)-2-(2-((R)-1-(tert-butoxycarbonylamino)-2-phenylethyl)thiazol-4-yl)-4-methyl-4,5-dihydrothiazole-4-carboxamido)-3-methylbutanoyloxy)-7-(tritylthio)hept-4-enoate

C₄₇H₄₈N₄O₄S₃

(5R,8S,11S)-8-isopropyl-11-(4-mercaptobut-1-enyl)-5-methyl-10-oxa-3,17-dithia-7,14,19,20-tetraazatricyclo[14.2.1.1(2,5)]icosa-1⁽¹⁸⁾,2⁽²⁰⁾,16⁽¹⁹⁾-triene-6,9,13-trione

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