methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

Base Information

Chemical Name:methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate
CAS No.:1314795-28-2
Molecular Formula:C₂₃H₃₃NO₅S
Molecular Weight:435.585
Hs Code.:

Synonyms:methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

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Chemical Property of methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

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Technology Process of methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

There total 12 articles about methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate 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: 48.0%

: 1314795-26-0
methyl 3-((3r,6r)-1-oxaspiro[2.5]octan-6-ylamino)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate

: 86087-23-2,84921-89-1,864447-89-2
(S)-3-hydroxytetyrahydrofurane

: 1314795-28-2
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

Guidance literature:: (S)-3-hydroxytetyrahydrofurane; With potassium tert-butylate; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 0.25h;

methyl 3-((3r,6r)-1-oxaspiro[2.5]octan-6-ylamino)-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylate; In 1-methyl-pyrrolidin-2-one; at 40 ℃; for 24h;
DOI:10.1021/jm401420j

Reference yield:

: 1485470-44-7
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1s,4s)-4-(tetrahydrofuran-3-yloxy)cyclohexylamino)thiophene-2-carboxylate

: 1314795-28-2
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1,2-dichloro-ethane / 70 °C

2.1: lithium hydroxide / tetrahydrofuran; water / 20 °C

3.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.25 h / 20 °C

3.2: 3 h

4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0.25 h / 20 °C

4.2: 24 h / 40 °C

With potassium tert-butylate; sodium hydride; lithium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; water; dimethyl sulfoxide; 1,2-dichloro-ethane; mineral oil;
DOI:10.1021/jm401420j

Reference yield:

: 1263101-80-9
5-(3,3-dimethyl-but-1-ynyl)-3-(1,4-dioxa-spiro[4.5]dec-8-ylamino)-thiophene-2-carboxylic acid methyl ester

: 1314795-28-2
methyl 5-(3,3-dimethylbut-1-ynyl)-3-((1S,4r)-4-hydroxy-4-(((S)-tetrahydrofuran-3-yloxy)methyl)cyclohexylamino)thiophene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydrogenchloride / tetrahydrofuran; water; methanol / 40 °C

2.1: iron(III) chloride; triethylsilane / 0 - 20 °C

3.1: 1,2-dichloro-ethane / 70 °C

4.1: lithium hydroxide / tetrahydrofuran; water / 20 °C

5.1: sodium hydride / mineral oil; dimethyl sulfoxide / 0.25 h / 20 °C

5.2: 3 h

6.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0.25 h / 20 °C

6.2: 24 h / 40 °C

With hydrogenchloride; triethylsilane; iron(III) chloride; potassium tert-butylate; sodium hydride; lithium hydroxide; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane; mineral oil; 1.1: |Weinreb Ketone Synthesis;
DOI:10.1021/jm401420j