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

Base Information

• Chemical Name: (S)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic acid
• CAS No.: 123168-11-6
• Molecular Formula: C₃₁H₃₅NO₆S
• Molecular Weight: 549.688

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 9 articles about (S)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ⁶-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic 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: 80.0%

(S)-2-phenylglycine (2935-35-5) + C23H27ClO4S (93962-31-3) → (S)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic acid (123168-11-6)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1021/jo00286a019

Reference yield:

diphenyl sulfide (139-66-2) → (S)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic acid (123168-11-6)

Guidance literature:

Multi-step reaction with 6 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

With n-butyllithium; 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)-(2,7-Di-tert-butyl-10,10-dioxo-9,10-dihydro-10λ6-thioxanthen-9-ylmethoxycarbonylamino)-phenyl-acetic acid (123168-11-6)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo00286a019

upstream raw materials:

(S)-2-phenylglycine

C₂₃H₂₇ClO₄S

thioxanthene

diphenyl sulfide

Downstream raw materials:

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

(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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