(S)-1-CBZ-AMINO-2-BOC-AMINO-3-PHENYL-PROPANE

Base Information

• Chemical Name: (S)-1-CBZ-AMINO-2-BOC-AMINO-3-PHENYL-PROPANE
• CAS No.: 835916-04-6
• Molecular Formula: C22H28N2O4
• Molecular Weight: 384.46900
• Hs Code.: 2922499990
• Mol file: 835916-04-6.mol

Synonyms:(S)-1-CBZ-AMINO-2-BOC-AMINO-3-PHENYL-PROPANE;[(2S)-2-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-3-PHENYLPROPYL]-CARBAMIC ACID PHENYLMETHYL ESTER;[(2R)-2-[[(tert-Butoxy)carbonyl]amino]-3-phenylpropyl]carbamic acid benzyl ester

Chemical Property of (S)-1-CBZ-AMINO-2-BOC-AMINO-3-PHENYL-PROPANE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 562.325oC at 760 mmHg
• PKA: 12.20±0.46(Predicted)
• Flash Point: 293.884°C
• PSA: 76.66000
• Density: 1.130
• LogP: 4.83060

Purity/Quality:

99% ^*data from raw suppliers

[(2S)-2-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-phenylpropyl]-carbamicacid phenylmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1-CBZ-AMINO-2-BOC-AMINO-3-PHENYL-PROPANE

There total 1 articles about (S)-1-CBZ-AMINO-2-BOC-AMINO-3-PHENYL-PROPANE 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: 77.0%

benzyl chloroformate (501-53-1,94274-21-2) + (2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropylamine (185384-16-1,179051-72-0) → (2-tert-butoxycarbonylamino-3-phenyl-propyl)-carbamic acid benzyl ester (835916-04-6)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jm040832y

Reference yield: 99.0%

(2-tert-butoxycarbonylamino-3-phenyl-propyl)-carbamic acid benzyl ester (835916-04-6) → (2(R)-amino-3-phenylpropyl)carbamic acid benzyl ester hydrochloride

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; methanol; for 1h;

DOI:10.1021/jm040832y

Reference yield:

(2-tert-butoxycarbonylamino-3-phenyl-propyl)-carbamic acid benzyl ester (835916-04-6) → N-[(2S,5S,8R,12R)-5,8-Dibenzyl-2-(1H-indol-3-ylmethyl)-3,6,11,14-tetraoxo-1,4,7,10-tetraaza-cyclotetradec-12-yl]-succinamic acid (835916-36-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 99 percent / HCl / methanol; dioxane / 1 h

2.1: HOBt; EDC*HCl / acetonitrile / 0.5 h / 0 °C

2.2: Et₃N / acetonitrile / 3 h / 20 °C

3.1: 30 g / HCl / methanol; dioxane / 8 h / 20 °C

4.1: HOBt; EDC*HCl / dimethylformamide / 0.25 h

4.2: Et₃N / dimethylformamide / 2 h / 20 °C

5.1: HCl / methanol; dioxane / 5.5 h / 20 °C

6.1: HOBt; EDC*HCl / dimethylformamide / 0.25 h

6.2: 69 percent / Et₃N / dimethylformamide / 4 h / 20 °C

7.1: 93 percent / H₂ / Pd/C / dimethylformamide; H₂O / 6 h

8.1: 62 percent / HOBt; EDC*HCl / dimethylformamide / 2.5 h / 20 °C

9.1: HCl / methanol; dioxane / 20 h / 20 °C

10.1: DMF / acetonitrile / 2 h / 20 °C

With hydrogenchloride; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm040832y

upstream raw materials:

benzyl chloroformate

(2R)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropylamine

Downstream raw materials:

(2-(R)-{2-(S)-[2-(S)-amino-3-(1H-indol-3-yl)propionylamino]-3-phenylpropionylamino}-3-phenylpropyl)carbamic acid benzyl ester

(2-{2-[2-tert-butoxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-3-phenyl-propionylamino}-3-phenyl-propyl)-carbamic acid benzyl ester

(12R)-amino-(5S,8R)-dibenzyl-2-(S)-(1H-indol-3-ylmethyl)-1,4,7,10-tetraaza-cyclotetradecane-3,6,11,14-tetraone

(2S,5S,8R,13S)-13-Amino-5,8-dibenzyl-2-(1H-indol-3-ylmethyl)-1,4,7,10-tetraaza-cyclotetradecane-3,6,11,14-tetraone

Refernces