(2E,4S)-4-[(tert-Butyloxycarbonyl)aMino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester

Base Information

• Chemical Name: (2E,4S)-4-[(tert-Butyloxycarbonyl)aMino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester
• CAS No.: 328086-54-0
• Molecular Formula: C16H26N2O5
• Molecular Weight: 326.393
• Mol file: 328086-54-0.mol

Synonyms:tert-butyl (S,E)-4-(ethoxycarbonyl)-1-((S)-2-oxopyrrolidin-3-yl)but-3-en-2-ylcarbamate;(S,E)-ethyl 4-(tert-butoxycarbonylamino)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate;(E)-(S)-4-tert-Butoxycarbonylamino-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester;(2E,4S)-4-[(tert-Butyloxycarbonyl)amino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester;4S-tert-butoxycarbonylamino-5-(2-oxopyrrolidin-3S-yl)pent-2-enoic acid ethyl ester;4-tert-butoxycarbonylamino-5-(2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester;

Chemical Property of (2E,4S)-4-[(tert-Butyloxycarbonyl)aMino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester

Chemical Property:

• Boiling Point: 515.4±35.0 °C(Predicted)
• PKA: 11.14±0.46(Predicted)
• PSA: 93.73000
• Density: 1.111±0.06 g/cm3(Predicted)
• LogP: 2.24490
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol

Purity/Quality:

(2E,4S)-4-[(tert-Butyloxycarbonyl)amino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoicAcidEethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2E,4S)-4-[(tert-Butyloxycarbonyl)aMino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester is used in the preparation of Rhinovirus protease inhibitors.

Technology Process of (2E,4S)-4-[(tert-Butyloxycarbonyl)aMino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester

There total 26 articles about (2E,4S)-4-[(tert-Butyloxycarbonyl)aMino]-5-[(3S)-2-oxo-3-pyrrolidinyl]-2-pentenoic Acid Eethyl Ester 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:

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + tert-butyl ((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate (1025451-28-8) → (2E,4S)-4-(tert-butoxycarbonylamino)-5-[(3'S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic acid ethyl ester (328086-54-0)

Guidance literature:

In dichloromethane; at 23 ℃; for 2h;

DOI:10.1021/jm050548m

Reference yield:

dimethyl (S)-2-((tert-butoxycarbonyl)amino)-4-methylenepentanedioate (95049-80-2) + tert-butyl ((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate (1025451-28-8) → (2E,4S)-4-(tert-butoxycarbonylamino)-5-[(3'S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic acid ethyl ester (328086-54-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

Reference yield:

dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate (59279-60-6,130622-05-8,861658-15-3) → (2E,4S)-4-(tert-butoxycarbonylamino)-5-[(3'S)-2'-oxo-3'-pyrrolidinyl]-2-pentenoic acid ethyl ester (328086-54-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiN(SiMe₃)2 / tetrahydrofuran / 3 h / -78 °C

1.2: 82 percent / tetrahydrofuran / 3.5 h

2.1: H₂ / PtO₂ / methanol; CHCl₃ / 12 h / 25 °C

3.1: NaOAc / methanol; CHCl₃ / 12 h / Heating

4.1: 89 percent / NaBH₄; LiCl / ethanol; tetrahydrofuran / 18 h / 25 °C

5.1: 89 percent / pyridine suflur trioxide complex (1:1); Et₃N / dimethylsulfoxide; CH₂Cl₂ / 3 h / -10 °C

6.1: tetrahydrofuran / 1 h / -78 °C

With sodium tetrahydroborate; hydrogen; sodium acetate; sulfur trioxide pyridine complex; triethylamine; lithium chloride; lithium hexamethyldisilazane; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; dimethyl sulfoxide; 6.1: Wittig-Emmons reaction;

DOI:10.1016/j.bmc.2005.05.065

upstream raw materials:

ethyl bromoacetate

tert-butyl ((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)carbamate

ethyl (triphenylphosphoranylidene)acetate

ethyl-3->-E-propenoate

Downstream raw materials:

(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

(E)-(S)-4-{(2R,4S,5S)-2-Benzyl-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-heptanoylamino}-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

(E)-(S)-4-[(2R,4S,5S)-2-Benzyl-5-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-heptanoylamino]-5-((S)-2-oxo-pyrrolidin-3-yl)-pent-2-enoic acid ethyl ester

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