(S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester
• CAS No.: 123168-19-4
• Molecular Formula: C₃₉H₅₀N₂O₇S
• Molecular Weight: 690.901

Synonyms:(S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

Chemical Property of (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

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Technology Process of (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester

There total 12 articles about (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic 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: 84.0%

methyl (L)-leucinate hydrochloride (7517-19-3) + ((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethyl ester (123168-15-0) → (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester (123168-19-4)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo00286a019

Reference yield:

diphenyl sulfide (139-66-2) → (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester (123168-19-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / ferric chloride / CH₂Cl₂ / 72 h / Heating

2: 37 percent / tin(IV) chloride / CH₂Cl₂ / 12 h / Ambient temperature

3: 1.) n-butyllithium / 1.) THF, -75 deg C, 30 min, 2.) reflux, 30 min

4: 55 percent / 30percent H₂O₂, acetic acid / 4 h / 100 °C

5: 87 percent / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) room temperature, 4 h

6: 70 percent / 10percent aq. Na₂CO₃ / tetrahydrofuran / 2 h / 0 °C

7: N-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 0 - 20 °C

With n-butyllithium; dihydrogen peroxide; iron(III) chloride; tin(IV) chloride; sodium carbonate; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00286a019

Reference yield:

bis(4-tert-butylphenyl) sulfide (52908-55-1) → (S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-3-phenyl-propionylamino]-4-methyl-pentanoic acid methyl ester (123168-19-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 37 percent / tin(IV) chloride / CH₂Cl₂ / 12 h / Ambient temperature

2: 1.) n-butyllithium / 1.) THF, -75 deg C, 30 min, 2.) reflux, 30 min

3: 55 percent / 30percent H₂O₂, acetic acid / 4 h / 100 °C

4: 87 percent / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) room temperature, 4 h

5: 70 percent / 10percent aq. Na₂CO₃ / tetrahydrofuran / 2 h / 0 °C

6: N-hydroxybenzotriazole, dicyclohexylcarbodiimide / tetrahydrofuran / 0 - 20 °C

With n-butyllithium; dihydrogen peroxide; tin(IV) chloride; sodium carbonate; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00286a019

upstream raw materials:

methyl (L)-leucinate hydrochloride

((S)-1-Chlorocarbonyl-2-phenyl-ethyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl ester

thioxanthene

diphenyl sulfide

Downstream raw materials:

L-phenylalanyl-L-leucine methyl ester

9-methylene-2,7-di-tert-butyl-10,10-dioxythioxanthene

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