(R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 136057-28-8
• Molecular Formula: C₅₇H₆₈N₄O₁₂
• Molecular Weight: 1001.19
• Mol file: 136057-28-8.mol

Synonyms:

Chemical Property of (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 21 articles about (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

methyl (E)-4-bromocinnamate (3650-78-0,84878-00-2,71205-17-9) → (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (136057-28-8)

Guidance literature:

Multi-step reaction with 10 steps

2: 91 percent / H₂ / 10percent Pd/C / methanol / 16 h

3: 100 percent / LiOH / tetrahydrofuran / 17 h / Ambient temperature

4: Et₃N / diethyl ether / 2 h / 0 °C

5: 1) BuLi / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, diethylether, RT, 1 h

6: 1) potassium hexamethyldisilylamide, 2) trisyl azide / 1) toluene, THF, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 2 min.

7: 515 mg / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 0.67 h / 0 °C

8: N,N-dicyclohexylcarbodiimide (DCC) hydrochloride / CH₂Cl₂ / 0.83 h / Ambient temperature

9: 477 mg / 1) H₂, 2) HCl / 10percent Pd/C / trifluoroacetic acid; methanol / 2 h

10: N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) hydrochloride / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; n-butyllithium; N,N'-dicyclohexyl-carbodiimide hydrochloride; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; trifluoroacetic acid;

Reference yield:

trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) → (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (136057-28-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / SOCl₂ / 3 h / Heating

3: 91 percent / H₂ / 10percent Pd/C / methanol / 16 h

4: 100 percent / LiOH / tetrahydrofuran / 17 h / Ambient temperature

5: Et₃N / diethyl ether / 2 h / 0 °C

6: 1) BuLi / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, diethylether, RT, 1 h

7: 1) potassium hexamethyldisilylamide, 2) trisyl azide / 1) toluene, THF, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 2 min.

8: 515 mg / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 0.67 h / 0 °C

9: N,N-dicyclohexylcarbodiimide (DCC) hydrochloride / CH₂Cl₂ / 0.83 h / Ambient temperature

10: 477 mg / 1) H₂, 2) HCl / 10percent Pd/C / trifluoroacetic acid; methanol / 2 h

11: N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) hydrochloride / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; n-butyllithium; thionyl chloride; N,N'-dicyclohexyl-carbodiimide hydrochloride; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; trifluoroacetic acid;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-4-{3-[4-((R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (136057-28-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / NaOH / 2-methyl-propan-2-ol / 17 h / Ambient temperature

2: 89 percent / LiBH₄ / diethyl ether / 7 h / 0 °C

3: 91 percent / toluene-p-sulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

5: 91 percent / H₂ / 10percent Pd/C / methanol / 16 h

6: 100 percent / LiOH / tetrahydrofuran / 17 h / Ambient temperature

7: Et₃N / diethyl ether / 2 h / 0 °C

8: 1) BuLi / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, diethylether, RT, 1 h

9: 1) potassium hexamethyldisilylamide, 2) trisyl azide / 1) toluene, THF, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 2 min.

10: 515 mg / H₂O₂, LiOH*H₂O / tetrahydrofuran; H₂O / 0.67 h / 0 °C

11: N,N-dicyclohexylcarbodiimide (DCC) hydrochloride / CH₂Cl₂ / 0.83 h / Ambient temperature

12: 477 mg / 1) H₂, 2) HCl / 10percent Pd/C / trifluoroacetic acid; methanol / 2 h

13: N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide (EDC) hydrochloride / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; lithium hydroxide; sodium hydroxide; lithium borohydride; n-butyllithium; N,N'-dicyclohexyl-carbodiimide hydrochloride; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; trifluoroacetic acid; tert-butyl alcohol;

upstream raw materials:

(R)-2-(((benzyloxy)carbonyl)amino)-2-(4-hydroxyphenyl)acetic acid

di-tert-butyl dicarbonate

methyl (E)-4-bromocinnamate

trans-4-bromocinnamic acid