(3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid

Base Information

• Chemical Name: (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid
• CAS No.: 464170-05-6
• Molecular Formula: C₂₆H₂₇ClN₂O₃
• Molecular Weight: 450.965

Synonyms:(3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid

Chemical Property of (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid

Chemical Property:

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Technology Process of (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid

There total 5 articles about (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic 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: 60.0%

6-bromo-2,3-dihydro-1-benzofuran (189035-22-1) + 2-(N-benzylisopropylamino)-6-chloro-5-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine (464170-04-5) → (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid (464170-05-6)

Guidance literature:

6-bromo-2,3-dihydro-1-benzofuran; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

2-(N-benzylisopropylamino)-6-chloro-5-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

With sulfuric acid; In 1,4-dioxane; water; at 100 ℃; for 1.5h;

DOI:10.1016/S0040-4020(02)00280-6

Reference yield:

2,6-dichloropyridine (2402-78-0) → (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid (464170-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; toluene / -64 - 0 °C

1.2: 99 percent / hexane; toluene / 4 - 20 °C

2.1: POCl₃ / 8 - 20 °C

2.2: 99 percent / toluene / 8 h / 70 °C

3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: ClPO(OEt)2 / tetrahydrofuran; hexane / -78 - 0 °C

3.3: tetrahydrofuran; hexane / 0.5 h / 0 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 60 percent / conc. H₂SO₄ / dioxane; H₂O / 1.5 h / 100 °C

With n-butyllithium; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; hexane; toluene; 2.1: Vilsmeier formylation;

DOI:10.1016/S0040-4020(02)00280-6

Reference yield:

Benzyl-isopropyl-amin (102-97-6) → (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid (464170-05-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / hexane; toluene / -64 - 0 °C

1.2: 99 percent / hexane; toluene / 4 - 20 °C

2.1: POCl₃ / 8 - 20 °C

2.2: 99 percent / toluene / 8 h / 70 °C

3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: ClPO(OEt)2 / tetrahydrofuran; hexane / -78 - 0 °C

3.3: tetrahydrofuran; hexane / 0.5 h / 0 °C

4.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

4.2: tetrahydrofuran; hexane / 1 h / -78 °C

4.3: 60 percent / conc. H₂SO₄ / dioxane; H₂O / 1.5 h / 100 °C

With n-butyllithium; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; hexane; toluene; 2.1: Vilsmeier formylation;

DOI:10.1016/S0040-4020(02)00280-6

upstream raw materials:

6-bromo-2,3-dihydro-1-benzofuran

2-(N-benzylisopropylamino)-6-chloro-5-{(E)-[2-(4S,5S)-4-methoxymethyl-5-(4-methylthiophenyl)-4,5-dihydro-1,3-oxazol-2-yl]vinyl}pyridine

2,6-dichloropyridine

Benzyl-isopropyl-amin

Downstream raw materials:

tert-butyl (3S)-3-{6-(N-benzyl-N-isopropylamino)-2-(S)-hydroxy[4-methoxy-2-(4-methoxybenzyloxymethyl)phenyl]-methyl-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

tert-butyl (3S)-3-{6-(N-benzyl-N-isopropylamino)-2-[4-methoxy-2-(4-methoxy-benzyloxymethyl)benzoyl]-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

tert-butyl (5S,6R,7R)-2-(N-benzyl-N-isopropylamino)-5-(2,3-dihydro-1-benzofuran-6-yl)-7-[4-methoxy-2-(4-methoxybenzyloxymethyl)phenyl]-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

tert-butyl (5S,6R,7R)-(+)-5-(2,3-dihydrobenzo[b]furan-6-yl)-7-(2-hydroxymethyl-4-methoxyphenyl)-2-(N-isopropylamino)-6,7-dihydro-5H-cyclopenta[b]pyridine-6-carboxylate

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