tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Base Information

• Chemical Name: tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate
• CAS No.: 464170-06-7
• Molecular Formula: C₃₀H₃₅ClN₂O₃
• Molecular Weight: 507.072

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 6 articles about tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate 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:

tert-butyl alcohol (75-65-0) + (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoic acid (464170-05-6) → tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate (464170-06-7)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; at 20 ℃; for 12h;

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

Reference yield:

2,6-dichloropyridine (2402-78-0) → tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate (464170-06-7)

Guidance literature:

Multi-step reaction with 5 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

5.1: EDC; 4-dimethylaminopyridine / tetrahydrofuran / 12 h / 20 °C

With dmap; n-butyllithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 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) → tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-chloro-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate (464170-06-7)

Guidance literature:

Multi-step reaction with 5 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

5.1: EDC; 4-dimethylaminopyridine / tetrahydrofuran / 12 h / 20 °C

With dmap; n-butyllithium; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; hexane; toluene; 2.1: Vilsmeier formylation;

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

upstream raw materials:

tert-butyl alcohol

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

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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