(R)-4-{3-[4-((R)-2-Azido-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-Azido-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.: 136057-27-7
• Molecular Formula: C₄₁H₅₃N₅O₈
• Molecular Weight: 743.901
• Mol file: 136057-27-7.mol

Synonyms:

Chemical Property of (R)-4-{3-[4-((R)-2-Azido-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-Azido-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 18 articles about (R)-4-{3-[4-((R)-2-Azido-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-Azido-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (136057-27-7)

Guidance literature:

Multi-step reaction with 8 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

With lithium hydroxide; n-butyllithium; N,N'-dicyclohexyl-carbodiimide hydrochloride; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

Reference yield:

trans-4-bromocinnamic acid (1200-07-3,5676-63-1,17916-60-8) → (R)-4-{3-[4-((R)-2-Azido-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (136057-27-7)

Guidance literature:

Multi-step reaction with 9 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

With lithium hydroxide; n-butyllithium; thionyl chloride; N,N'-dicyclohexyl-carbodiimide hydrochloride; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-4-{3-[4-((R)-2-Azido-2-{[(S)-tert-butoxycarbonyl-(4-tert-butoxy-phenyl)-methyl]-carbamoyl}-ethyl)-phenoxy]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (136057-27-7)

Guidance literature:

Multi-step reaction with 11 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

With 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; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol;

upstream raw materials:

(S)-4-tert-butoxyphenylglycine tert-butyl ester hydrochloride

di-tert-butyl dicarbonate

methyl (E)-4-bromocinnamate

trans-4-bromocinnamic acid