3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid

Base Information

• Chemical Name: 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid
• CAS No.: 171550-02-0
• Molecular Formula: C₂₂H₂₂N₂O₄
• Molecular Weight: 378.428

Synonyms:3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid

Chemical Property of 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid

Chemical Property:

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Technology Process of 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid

There total 3 articles about 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic 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-Isocyanato-3-methylene-cyclobutane → 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid (171550-02-0)

Guidance literature:

Multi-step reaction with 3 steps

1: DPPA

2: 19.5 percent / H₂; (Ph₃P)3RhCl / toluene / 18 h / 70 °C / 76000 Torr

3: 1percent aq. H₂SO₄ / 7 h / 90 °C

With Wilkinson's catalyst; diphenyl-phosphinic acid; hydrogen; In toluene;

DOI:10.1021/jm000956k

Reference yield:

N-(benzyloxycarbonyl)-3-methylenecyclobutanamine (130368-98-8) → 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid (171550-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 19.5 percent / H₂; (Ph₃P)3RhCl / toluene / 18 h / 70 °C / 76000 Torr

2: 1percent aq. H₂SO₄ / 7 h / 90 °C

With Wilkinson's catalyst; hydrogen; In toluene;

DOI:10.1021/jm000956k

Reference yield:

p-carboxymethylphenylhydrazine hydrochloride (57412-05-2,65476-32-6) + trans-N-(benzyloxycarbonyl)cyclobutanamine-3-acetaldehyde (171549-94-3) → 3-[trans-N-(benzyloxycarbonyl)cyclobutanamine]-1H-indol-5-ylacetic acid (171550-02-0)

Guidance literature:

With 1percent aq. H₂SO₄; at 90 ℃; for 7h;

DOI:10.1021/jm000956k

upstream raw materials:

p-carboxymethylphenylhydrazine hydrochloride

trans-N-(benzyloxycarbonyl)cyclobutanamine-3-acetaldehyde

N-(benzyloxycarbonyl)-3-methylenecyclobutanamine

Downstream raw materials:

{3-[5-(benzylcarbamoyl-methyl)-1H-indol-3-yl]-cyclobutyl}-carbamic acid benzyl ester

[3-(5-carbamoylmethyl-1H-indol-3-yl)-cyclobutyl]-carbamic acid benzyl ester

{3-[5-(5-methyl-2H-[1,2,4]triazol-3-ylmethyl)-1H-indol-3-yl]-cyclobutyl}-carbamic acid benzyl ester

{3-[5-(3-methyl-[1,2,4]oxadiazol-5-ylmethyl)-1H-indol-3-yl]-cyclobutyl}-carbamic acid benzyl ester

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