tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-butoxycarbonyl-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-butoxycarbonyl-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate
CAS No.:464170-07-8
Molecular Formula:C₃₅H₄₄N₂O₅
Molecular Weight:572.745
Hs Code.:

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

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

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

There total 9 articles about tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-butoxycarbonyl-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: 87.0%

: 201230-82-2
carbon monoxide

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

: 71-36-3
butan-1-ol

: 464170-07-8
tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-butoxycarbonyl-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Guidance literature:: With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium acetate; In toluene; at 120 ℃; for 18h; under 760 Torr;
DOI:10.1016/S0040-4020(02)00280-6

Reference yield:

: C₈H₉BO₃

: 913648-54-1
6-(N-benzyl-N-isopropylamino)-3-(2-tert-butoxycarbonylvinyl)pyridine-2-carboxylic acid butyl ester

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

: 464170-07-8
tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-butoxycarbonyl-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Guidance literature:: With potassium hydroxide; (R,R)-chiraphos; di(norbornadiene)rhodium(I) tetrafluoroborate; In 1,4-dioxane; water; at 50 ℃; for 14h; Title compound not separated from byproducts;
DOI:10.1016/j.tet.2006.07.075

Reference yield:

: 2402-78-0
2,6-dichloropyridine

: 464170-07-8
tert-butyl (3S)-3-[6-(N-benzyl-N-isopropylamino)-2-butoxycarbonyl-3-pyridinyl]-3-(2,3-dihydro-1-benzofuran-6-yl)propanoate

Guidance literature:: Multi-step reaction with 5 steps

1: BuLi

2: POCl₃

3: 85 percent / tetrahydrofuran / 5 h / 40 °C

4: 87 percent / DPPF; AcONa*3H₂O / Pd(OAc)2 / toluene / 16 h / 120 °C / 760 Torr

5: KOH; (R,R)-chiraphos / [Rh(nbd)2]BF₄ / dioxane; H₂O / 14 h / 50 °C

With 1,1'-bis-(diphenylphosphino)ferrocene; potassium hydroxide; n-butyllithium; (R,R)-chiraphos; sodium acetate; trichlorophosphate; palladium diacetate; di(norbornadiene)rhodium(I) tetrafluoroborate; In tetrahydrofuran; 1,4-dioxane; water; toluene;
DOI:10.1016/j.tet.2006.07.075