(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

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Chemical Name:(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate
CAS No.:799270-24-9
Molecular Formula:C₃₁H₄₄FN₃O₇
Molecular Weight:589.705
Hs Code.:

Synonyms:(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

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Chemical Property of (S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

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Technology Process of (S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

There total 32 articles about (S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate 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: 79.0%

: 223526-67-8
(2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid

: 328086-61-9
ethyl (S,E)-4-((tert-butoxycarbonyl)amino)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

: 799270-24-9
(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

Guidance literature:: With N,N-diethyl-N-isopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;
DOI:10.1016/j.tetlet.2004.08.179

Reference yield:

: 18125-46-7
(R)-4-fluorophenylalanine

: 799270-24-9
(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: hydrogen bromide; sodium nitrite / 11 h / 0 - 20 °C

2.1: sulfuric acid / 2 h / 70 °C

3.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 8 h / 80 °C

4.1: trifluoroacetic acid / dichloromethane / 4 h / 30 °C

5.1: palladium on activated charcoal; hydrogen / methanol / 25 °C

6.1: triethylamine / 2 h

7.1: sodium hydroxide / ethanol; water / 1 h / 20 °C

8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 20 °C

8.2: 6 h / 20 °C

With sulfuric acid; palladium on activated charcoal; hydrogen bromide; hydrogen; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; potassium iodide; sodium hydroxide; sodium nitrite; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1007/s11426-011-4478-5

Reference yield:

: 72-18-4,25609-85-2,7004-03-7,921-10-8
L-valine

: 799270-24-9
(S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate

Guidance literature:: Multi-step reaction with 10 steps

1: K₂CO₃

2: LAH / tetrahydrofuran / 0 °C

3: 90 percent / H₂ / Pd(OH)2/C / ethyl acetate

4: 95 percent / Et₃N

5: NaOH

6: 63 percent / LiHMDS / -78 °C

7: LiOH / 1,2-dimethoxy-ethane; H₂O

8: PCC

9: 79 percent / HATU; i-PrNEt₂

With lithium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; N,N-diethyl-N-isopropylamine; hydrogen; potassium carbonate; triethylamine; pyridinium chlorochromate; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hexamethyldisilazane; palladium dihydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water; ethyl acetate; 3: Swern oxidation;
DOI:10.1016/j.tetlet.2004.08.179