{2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 218912-15-3
• Molecular Formula: C₂₃H₃₈Br₂N₄O₃Si
• Molecular Weight: 606.473
• Mol file: 218912-15-3.mol

Synonyms:{2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Chemical Property of {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester

There total 11 articles about {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethylamine (218912-14-2) → {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester (218912-15-3)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 4h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

methyl 3,5-dibromo-4-aminobenzoate (3282-10-8) → {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester (218912-15-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

2.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

2.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

3.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

4.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

5.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

6.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

7.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

8.1: 78 percent / Ph₃P; H₂O / tetrahydrofuran / 3 h / 60 °C

9.1: 95 percent / Et₃N / CH₂Cl₂ / 4 h / 25 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; AD-α; diphenylphosphoranyl azide; water; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Reduction / 2.1: Diazotization / 2.2: Substitution / 3.1: Oxidation / 4.1: Condensation / 5.1: Addition / 6.1: Etherification / 7.1: Substitution / 8.1: Reduction / 9.1: Acylation;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → {2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethyl}-carbamic acid tert-butyl ester (218912-15-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 100 percent / SOCl₂ / 2 h / Heating

2.1: 98 percent / Br₂; AcOH / 0.5 h / 25 °C

3.1: 95 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4.1: NaNO₂; aq. HCl / acetic acid / 0.5 h / 0 °C

4.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

5.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

6.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

7.1: AD-α; H2O / 2-methyl-propan-2-ol / 6 h / 25 °C

8.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

9.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

10.1: 78 percent / Ph₃P; H₂O / tetrahydrofuran / 3 h / 60 °C

11.1: 95 percent / Et₃N / CH₂Cl₂ / 4 h / 25 °C

With 1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; n-butyllithium; thionyl chloride; AD-α; diphenylphosphoranyl azide; water; bromine; acetic acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Esterification / 2.1: Bromination / 3.1: Reduction / 4.1: Diazotization / 4.2: Substitution / 5.1: Oxidation / 6.1: Condensation / 7.1: Addition / 8.1: Etherification / 9.1: Substitution / 10.1: Reduction / 11.1: Acylation;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2602::AID-CHEM2602>3.0.CO;2-X

upstream raw materials:

di-tert-butyl dicarbonate

2-(tert-butyl-dimethyl-silanyloxy)-1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-ethylamine

methyl 3,5-dibromo-4-aminobenzoate

4-amino-benzoic acid

Downstream raw materials:

(2S,3R)-2-[(R)-2-{(R)-2-tert-Butoxycarbonylamino-2-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-(4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(3-chloro-4-hydroxy-phenyl)-propionic acid ethyl ester

tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid

{1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester