2-[(2S)-1-[(1,1-diMethylethoxy)carbonyl]2-pyrrolidinyl]-4-thiazolecarboxylic acid

Base Information

• Chemical Name: 2-[(2S)-1-[(1,1-diMethylethoxy)carbonyl]2-pyrrolidinyl]-4-thiazolecarboxylic acid
• CAS No.: 251349-54-9
• Molecular Formula: C₁₃H₁₈N₂O₄S
• Molecular Weight: 298.363
• Mol file: 251349-54-9.mol

Synonyms:2-[(2S)-1-[(1,1-diMethylethoxy)carbonyl]2-pyrrolidinyl]-4-thiazolecarboxylic acid;Antibiotic-5d;2-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-1,3-thiazole-4-carboxylic acid

Chemical Property of 2-[(2S)-1-[(1,1-diMethylethoxy)carbonyl]2-pyrrolidinyl]-4-thiazolecarboxylic acid

Chemical Property:

• Boiling Point: 459.8±35.0 °C(Predicted)
• PKA: 3.73±0.10(Predicted)
• PSA: 107.97000
• Density: 1.317±0.06 g/cm3(Predicted)
• LogP: 2.85120

Purity/Quality:

99% ^*data from raw suppliers

Antibiotic-5d >98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-[(2S)-1-[(1,1-diMethylethoxy)carbonyl]2-pyrrolidinyl]-4-thiazolecarboxylic acid

There total 8 articles about 2-[(2S)-1-[(1,1-diMethylethoxy)carbonyl]2-pyrrolidinyl]-4-thiazolecarboxylic acid 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: 100.0%

ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate (212009-06-8) → (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylic acid (251349-54-9,1824349-18-9)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 2h;

Reference yield:

tert‐butyl (S)‐2‐carbamothioylpyrrolidine‐1‐carboxylate (117175-41-4,101410-18-8) → (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylic acid (251349-54-9,1824349-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KHCO₃ / 1,2-dimethoxy-ethane; dimethylformamide / 0.08 h / -12 °C

1.2: 61 percent / trifluoroacetic anhydride; collidine / 1,2-dimethoxy-ethane; dimethylformamide / 0.32 h / -12 °C

2.1: 93 percent / NaOH / tetrahydrofuran; H₂O / 5 h / 20 °C

With sodium hydroxide; potassium hydrogencarbonate; In tetrahydrofuran; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(03)00992-X

Reference yield:

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate (35150-07-3) → (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylic acid (251349-54-9,1824349-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Lawessons reagent / tetrahydrofuran / 5 h / 23 °C

2.1: potassium hydrogencarbonate / 1,2-dimethoxyethane / 0.5 h / 23 °C

2.2: 0 °C

3.1: sodium hydroxide; water / tetrahydrofuran / 3 h / 23 °C

3.2: 0 °C / pH 3

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

upstream raw materials:

ethyl (S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)thiazole-4-carboxylate

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

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

1-(tert-butoxycarbonyl)-L-proline

Downstream raw materials:

C₁₉H₂₁FN₂O₃S

C₃₁H₄₁FN₄O₅S

(2S)-N-[(1S)-1-cyclohexyl-2-[(2S)-2-[4-(4-fluorobenzoyl)-1,3-thiazol-2-yl]pyrrolidin-1-yl]-2-oxoethyl]-2-(methylamino)propanamide

Refernces

• 1、 -. "BIFUNCTIONAL COMPOUNDS FOR DEGRADING BTK VIA UBIQUITIN PROTEOSOME PATHWAY". Paragraph 0465-0466. . Retrieved 2021/05/15.
• 2、 -. "BIFUNCTIONAL COMPOUNDS FOR DEGRADING BTK VIA UBIQUITIN PROTEOSOME PATHWAY". Paragraph 0932; 0938. . Retrieved 2020/05/21.