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

Base Information

• Chemical Name: tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid
• CAS No.: 218912-17-5
• Molecular Formula: C₁₇H₂₂Br₂N₄O₄
• Molecular Weight: 506.194
• Mol file: 218912-17-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 19 articles about tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-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:

{1-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-2-hydroxy-ethyl}-carbamic acid tert-butyl ester → tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid (218912-17-5) + tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; In water; acetone; at 0 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2708::AID-ANIE2708>3.0.CO;2-E

Reference yield:

methyl 3,5-dibromo-4-aminobenzoate (3282-10-8) → tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid (218912-17-5)

Guidance literature:

Multi-step reaction with 11 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

10.1: 93 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / 0 °C

11.1: 75 percent / TEMPO; NaOCl; NaHCO₃ / KBr / acetone; H₂O / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; n-butyllithium; AD-α; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; potassium bromide; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; 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 / 10.1: Substitution / 11.1: Oxidation;

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

Reference yield:

(4-amino-3,5-dibromo-phenyl)-methanol (122063-98-3) → tert-butoxycarbonylamino-[3,5-dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetic acid (218912-17-5)

Guidance literature:

Multi-step reaction with 10 steps

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

1.2: 75 percent / KOH; H₂O / 0.5 h / 0 °C

2.1: 88 percent / PCC / CH₂Cl₂ / 2 h / 25 °C

3.1: 92 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -20 °C

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

5.1: 88 percent / imidazole / dimethylformamide / 5 h / 0 °C

6.1: 79 percent / Ph₃P; DEAD; diphenylphosphoryl azide / tetrahydrofuran / 2 h / 0 °C

7.1: 78 percent / Ph₃P; H₂O / tetrahydrofuran / 3 h / 60 °C

8.1: 95 percent / Et₃N / CH₂Cl₂ / 4 h / 25 °C

9.1: 93 percent / (n-Bu)4NF / tetrahydrofuran / 2 h / 0 °C

10.1: 75 percent / TEMPO; NaOCl; NaHCO₃ / KBr / acetone; H₂O / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; n-butyllithium; AD-α; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; triethylamine; triphenylphosphine; pyridinium chlorochromate; sodium nitrite; diethylazodicarboxylate; potassium bromide; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Diazotization / 1.2: Substitution / 2.1: Oxidation / 3.1: Condensation / 4.1: Addition / 5.1: Etherification / 6.1: Substitution / 7.1: Reduction / 8.1: Acylation / 9.1: Substitution / 10.1: Oxidation;

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

upstream raw materials:

methyl 3,5-dibromo-4-aminobenzoate

4-amino-benzoic acid

4-methoxycarbonyl aniline

(4-amino-3,5-dibromo-phenyl)-methanol

Downstream raw materials:

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

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

(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