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

Base Information

• Chemical Name: ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl ester
• CAS No.: 123168-14-9
• Molecular Formula: C₃₁H₃₄ClNO₅S
• Molecular Weight: 568.134

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

Chemical Property of ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl ester

Chemical Property:

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Technology Process of ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl ester

There total 10 articles about ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethyl 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: 70.0%

(S)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic acid (123168-11-6) → ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethyl ester (123168-14-9)

Guidance literature:

With thionyl chloride; In dichloromethane; for 0.5h; Heating;

DOI:10.1021/jo00286a019

Reference yield:

diphenyl sulfide (139-66-2) → ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethyl ester (123168-14-9)

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

7: 70 percent / thionyl chloride / CH₂Cl₂ / 0.5 h / Heating

With n-butyllithium; thionyl chloride; dihydrogen peroxide; iron(III) chloride; tin(IV) chloride; sodium carbonate; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00286a019

Reference yield:

bis(4-tert-butylphenyl) sulfide (52908-55-1) → ((S)-Chlorocarbonyl-phenyl-methyl)-carbamic acid 2,7-di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethyl ester (123168-14-9)

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

6: 70 percent / thionyl chloride / CH₂Cl₂ / 0.5 h / Heating

With n-butyllithium; thionyl chloride; dihydrogen peroxide; tin(IV) chloride; sodium carbonate; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00286a019

upstream raw materials:

(S)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic acid

thioxanthene

diphenyl sulfide

bis(4-tert-butylphenyl) sulfide

Downstream raw materials:

(S)-2-[(S)-2-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-2-phenyl-acetylamino]-propionic acid methyl ester

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