(S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester
• CAS No.: 211756-18-2
• Molecular Formula: C₁₈H₂₂N₂O₄
• Molecular Weight: 330.384

Synonyms:(S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

Chemical Property of (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester

There total 4 articles about (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl 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: 74.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride (35761-27-4,96192-93-7) → (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester (211756-18-2)

Guidance literature:

In water; for 12h; Ambient temperature;

DOI:10.1021/jm980071x

Reference yield:

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester (211756-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / HCl gas / 12 h / Ambient temperature

2: 74 percent / H₂O / 12 h / Ambient temperature

With hydrogenchloride; In water;

DOI:10.1021/jm980071x

Reference yield:

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine (16947-84-5,62234-36-0) → (S)-3-(2-Aza-bicyclo[2.2.1]hept-5-en-2-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester (211756-18-2)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / 0.17 h / Ambient temperature

2: 1.) CF₃COOH / 1.) CH₂Cl₂, RT, 20 min, 2.) H₂O, RT, 1 h

With trifluoroacetic acid; In diethyl ether;

DOI:10.1021/ja00029a031

upstream raw materials:

formaldehyd

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate

cyclopenta-1,3-diene

methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride

Downstream raw materials:

2-benzyloxycarbonylamino-3-methylamino-propionic acid methyl ester

[(S)-2-(Acetyl-methyl-amino)-1-hydroxymethyl-ethyl]-carbamic acid benzyl ester

(S)-3-(Acetyl-methyl-amino)-2-benzyloxycarbonylamino-propionic acid methyl ester

N^α-(benzyloxycarbonyl)-N^β-(tert-butoxycarbonyl)-N^β-methyl-L-α,β-diaminopropionic acid

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