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

Base Information

Chemical Name:tert-butyl (3S)-3-{2-[4-methoxy-2-(4-methoxy-benzyloxymethyl)benzoyl]-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate
CAS No.:494841-87-1
Molecular Formula:C₃₇H₃₉NO₇
Molecular Weight:609.719
Hs Code.:

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

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

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

There total 8 articles about tert-butyl (3S)-3-{2-[4-methoxy-2-(4-methoxy-benzyloxymethyl)benzoyl]-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: 88.0%

: 4-bromo-3-(4-methoxybenzyloxymethyl)anisole

: 494841-86-0
tert-butyl (3S)-3-(2-methoxycarbonyl-3-pyridinyl)-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

: 494841-87-1
tert-butyl (3S)-3-{2-[4-methoxy-2-(4-methoxy-benzyloxymethyl)benzoyl]-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Guidance literature:: 4-bromo-3-(4-methoxybenzyloxymethyl)anisole; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl (3S)-3-(2-methoxycarbonyl-3-pyridinyl)-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;
DOI:10.1248/cpb.50.1066

Reference yield:

: 6602-54-6
2-chloro-3-pyridinecarbonitrile

: 494841-87-1
tert-butyl (3S)-3-{2-[4-methoxy-2-(4-methoxy-benzyloxymethyl)benzoyl]-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: DIBAL-H / toluene / -40 - 0 °C

2.1: 117 g / aq. H₂SO₄ / 20 °C

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

3.2: ClPO(OEt)2 / hexane; tetrahydrofuran / 0.5 h / 0 °C

3.3: 92 percent / hexane; tetrahydrofuran / 0.5 h / 0 °C

4.1: n-BuLi; TMEDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.2: 76 percent Chromat_. / hexane; tetrahydrofuran / -78 °C

5.1: 11.2 g / aq. H₂SO₄ / dioxane / 1.5 h / 110 °C

6.1: 91 percent / EDCI; DMAP / tetrahydrofuran / 5 h / 20 °C

7.1: 97 percent / NaHCO₃; Pd(OAc)2; 1,1'-bis(diphenylphosphino)ferrocene / 18 h / 70 °C / 760 Torr

8.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

8.2: 88 percent / hexane; tetrahydrofuran / 0.17 h / -78 °C

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; diisobutylaluminium hydride; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; hexane; toluene;
DOI:10.1248/cpb.50.1066

Reference yield:

: 36404-88-3
2-chloro-3-carbaldehydepyridine

: 494841-87-1
tert-butyl (3S)-3-{2-[4-methoxy-2-(4-methoxy-benzyloxymethyl)benzoyl]-3-pyridinyl}-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: ClPO(OEt)2 / hexane; tetrahydrofuran / 0.5 h / 0 °C

1.3: 92 percent / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.1: n-BuLi; TMEDA / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 76 percent Chromat_. / hexane; tetrahydrofuran / -78 °C

3.1: 11.2 g / aq. H₂SO₄ / dioxane / 1.5 h / 110 °C

4.1: 91 percent / EDCI; DMAP / tetrahydrofuran / 5 h / 20 °C

5.1: 97 percent / NaHCO₃; Pd(OAc)2; 1,1'-bis(diphenylphosphino)ferrocene / 18 h / 70 °C / 760 Torr

6.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

6.2: 88 percent / hexane; tetrahydrofuran / 0.17 h / -78 °C

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sulfuric acid; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; hexane;
DOI:10.1248/cpb.50.1066