methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride

Base Information

• Chemical Name: methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride
• CAS No.: 142929-42-8
• Molecular Formula: C₃₄H₄₆N₄O₆S₂*ClH
• Molecular Weight: 707.355

Synonyms:

Chemical Property of methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride

There total 22 articles about methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride 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:

ethyl dihydrocinnamate (2021-28-5) → methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride (142929-42-8,143058-51-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 1.) LDA / 1.) a) cyclohexane, -78 deg C, 30 min, b) cyclohexane, HMPA, -78 deg C, 15 min, 2.) cyclohexane, HMPA, 30 min

2: 89 percent / H₂ / 4percent Pd/C / ethanol / 258.6 Torr

3: 85 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

4: DIBAL / diethyl ether; toluene / 0.75 h / -78 °C

5: diethyl ether; toluene; tetrahydrofuran / 0.5 h / -78 - 0 °C

6: 1.) NaH / 1.) ether, 0 deg C, 30 min, 2.) ether, 1 h

7: xylene / 2 h / Heating

8: 66 percent / aq. NaOH / ethanol / 48 h / Ambient temperature

9: 92 percent / 4-(dimethylamino)pyridine / CHCl₃ / 16 h / Ambient temperature

10: 1.58 g / conc. aq. H₂SO₄, CrO₃ / acetone / 3 h / 0 °C

11: HCl / CH₂Cl₂; dioxane / 0.25 h / Ambient temperature

12: 1-methylmorpholine (NMM) / tetrahydrofuran; dimethylformamide / 16 h / -23 - 20 °C

13: 1-methylmorpholine (NMM) / tetrahydrofuran / 0.75 h / -23 °C

14: 1-methylmorpholine (NMM) / tetrahydrofuran; dimethylformamide / 16 h / -23 - 20 °C

15: I₂ / aq. acetic acid / 0.33 h

16: HCl / CH₂Cl₂; dioxane / 0.25 h / Ambient temperature

17: 1-methylmorpholine (NMM) / tetrahydrofuran; dimethylformamide / 16 h / -23 - 20 °C

18: HCl / CH₂Cl₂; dioxane / 0.25 h / Ambient temperature

With 4-methyl-morpholine; chromium(VI) oxide; hydrogenchloride; dmap; sodium hydroxide; sulfuric acid; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetone; toluene; xylene;

DOI:10.1021/jm00094a002

Reference yield:

ethyl α-<(phenylmethoxy)methyl>benzenepropanoate (142929-53-1) → methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride (142929-42-8,143058-51-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 89 percent / H₂ / 4percent Pd/C / ethanol / 258.6 Torr

2: 85 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / Ambient temperature

3: DIBAL / diethyl ether; toluene / 0.75 h / -78 °C

4: diethyl ether; toluene; tetrahydrofuran / 0.5 h / -78 - 0 °C

5: 1.) NaH / 1.) ether, 0 deg C, 30 min, 2.) ether, 1 h

6: xylene / 2 h / Heating

7: 66 percent / aq. NaOH / ethanol / 48 h / Ambient temperature

8: 92 percent / 4-(dimethylamino)pyridine / CHCl₃ / 16 h / Ambient temperature

9: 1.58 g / conc. aq. H₂SO₄, CrO₃ / acetone / 3 h / 0 °C

10: HCl / CH₂Cl₂; dioxane / 0.25 h / Ambient temperature

11: 1-methylmorpholine (NMM) / tetrahydrofuran; dimethylformamide / 16 h / -23 - 20 °C

12: 1-methylmorpholine (NMM) / tetrahydrofuran / 0.75 h / -23 °C

13: 1-methylmorpholine (NMM) / tetrahydrofuran; dimethylformamide / 16 h / -23 - 20 °C

14: I₂ / aq. acetic acid / 0.33 h

15: HCl / CH₂Cl₂; dioxane / 0.25 h / Ambient temperature

16: 1-methylmorpholine (NMM) / tetrahydrofuran; dimethylformamide / 16 h / -23 - 20 °C

17: HCl / CH₂Cl₂; dioxane / 0.25 h / Ambient temperature

With 4-methyl-morpholine; chromium(VI) oxide; hydrogenchloride; dmap; sodium hydroxide; sulfuric acid; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide; acetone; toluene; xylene;

DOI:10.1021/jm00094a002

Reference yield:

(E)-(4S,13S)-7-Benzyl-13-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionylamino]-3,3,14,14-tetramethyl-6,12-dioxo-1,2-dithia-5,11-diaza-cyclotetradec-8-ene-4-carboxylic acid methyl ester → methyl 13α-<<2(S)-amino-3-(4-hydroxy-2,6-dimethylphenyl)-1-oxopropyl>amino>-3,3,14,14-tetramethyl-6,12-dioxo-7-(phenylmethyl)-1,2-dithia-5,11-diazacyclotetradec-8-ene-(4R)-4α-carboxylate hydrochloride (142929-42-8,143058-51-9)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; dichloromethane; for 0.25h; Ambient temperature;

DOI:10.1021/jm00094a002

upstream raw materials:

ethyl dihydrocinnamate

α-<3<<(1,1-dimethylethoxy)carbonyl>amino>-1(E)-propenyl>benzenepropanoic acid

(S)-N-Boc-2,6-dimethyltyrosine

ethyl α-(hydroxymethyl)benzenepropanoate

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