ethyl 2-(N-tert-butoxycarbonyl-2,4-pyrrolidinyl)thiazole-4-carboxylate

Base Information

• Chemical Name: ethyl 2-(N-tert-butoxycarbonyl-2,4-pyrrolidinyl)thiazole-4-carboxylate
• CAS No.: 212009-06-8
• Molecular Formula: C15H22N2O4S
• Molecular Weight: 326.41
• Mol file: 212009-06-8.mol

Synonyms:ethyl 2-(N-tert-butoxycarbonyl-2,4-pyrrolidinyl)thiazole-4-carboxylate;2-((S)-1-tert-Butoxycarbonyl-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

Chemical Property of ethyl 2-(N-tert-butoxycarbonyl-2,4-pyrrolidinyl)thiazole-4-carboxylate

Chemical Property:

• Melting Point: 102-104 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 430.6±35.0 °C(Predicted)
• PKA: 0.54±0.10(Predicted)
• PSA: 96.97000
• Density: 1.216±0.06 g/cm3(Predicted)
• LogP: 3.32970

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-((S)-1-tert-Butoxycarbonylpyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester 95%+ ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 2-(N-tert-butoxycarbonyl-2,4-pyrrolidinyl)thiazole-4-carboxylate

There total 8 articles about ethyl 2-(N-tert-butoxycarbonyl-2,4-pyrrolidinyl)thiazole-4-carboxylate 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: 92.0%

ethyl Bromopyruvate (70-23-5) + tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate (117175-41-4,101410-18-8) → ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate (212009-06-8)

Guidance literature:

ethyl Bromopyruvate; tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate; With potassium hydrogencarbonate; In 1,2-dimethoxyethane; at 23 ℃; for 0.5h;

With 2,3,4-lutidine; trifluoroacetic anhydride; In 1,2-dimethoxyethane; at 0 ℃;

Reference yield:

C15H24N2O5S → ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate (212009-06-8)

Guidance literature:

With di-tert-butyl dicarbonate; water; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 2h;

Reference yield:

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (35150-07-3) → ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate (212009-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / Lawesson's reagent / tetrahydrofuran / 3.5 h / 20 °C

2.1: KHCO₃ / 1,2-dimethoxy-ethane / 0.5 h / 20 °C

2.2: 76 percent / trifluoroacetic anhydride; 2,6-lutidine / 0.5 h / 0 °C

With Lawessons reagent; potassium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1021/ja017160a

upstream raw materials:

ethyl Bromopyruvate

tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate

(R)-2-carbamoylpyrrolidine-1-carboxylic acid tert-butyl ester

Downstream raw materials:

C₁₉H₂₁FN₂O₃S

2-(1-{2-[2-(2-{[1-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

2-((S)-1-{(S)-2-[(2S,3S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester

2-((S)-1-{(S)-2-[(2S,3S)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hydroxy-butyrylamino]-3-phenyl-propionyl}-pyrrolidin-2-yl)-thiazole-4-carboxylic acid ethyl ester