1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-
• CAS No.: 15761-39-4
• Molecular Formula: C10H17NO4
• Molecular Weight: 215.249
• Hs Code.: 2933 99 80
• Mol file: 15761-39-4.mol

Synonyms:BOC-L-PRO;1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-;(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylate;ZQEBQGAAWMOMAI-ZETCQYMHSA-M;AKOS028109273;1-tert-butyl(s)-pyrrolidine-1,2-dicarboxylate

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Chemical Property:

• Appearance/Colour: White to off-white microcrystalline powder
• Vapor Pressure: 2E-05mmHg at 25°C
• Melting Point: 133-135 °C(lit.)
• Refractive Index: -60 ° (C=2, AcOH)
• Boiling Point: 337.2 °C at 760 mmHg
• PKA: 4.01±0.20(Predicted)
• Flash Point: 157.7 °C
• PSA: 66.84000
• Density: 1.201 g/cm³
• LogP: 1.40840
• Storage Temp.: Store at RT.
• Solubility.: Soluble in acetic acid.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 214.10793299
• Heavy Atom Count: 15
• Complexity: 264

Purity/Quality:

98%min ^*data from raw suppliers

N-Boc-L-proline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCCC1C(=O)[O-]
• Isomeric SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)[O-]
• Description: N-Boc-L-proline is a synthetic intermediate. It has been used in the synthesis of enantioselective catalysts for aldol reactions and hepatitis C virus (HCV) NS5A inhibitors.
• Uses: N-Boc-L-proline is used as an intermediate in organic synthesis. It is also used to prepare daclatasvir, which inhibits the hepatitis C virus (HCV) non-structural 5A (NS5A) protein. Further, it is used as a drug in the treatment of hepatitis C virus (HCV).

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

There total 74 articles about 1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- 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%

1-(tert-butyl) 2-(2-oxo-2-phenylethyl) (S)-pyrrolidine-1,2-dicarboxylate (110345-80-7) → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 2h; Irradiation;

DOI:10.1021/acscatal.7b02117

Reference yield: 98.0%

(S)-N-(tert-butoxycarbonyl)proline methyl ester (59936-29-7) → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0)

Guidance literature:

(S)-N-(tert-butoxycarbonyl)proline methyl ester; With sodium hydroxide; In methanol; water; for 5h; Reflux;

With hydrogenchloride; In water; pH=3;

DOI:10.1016/j.tet.2010.03.002

Reference yield: 97.0%

C24H27NO5 → 1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 1h; Irradiation;

DOI:10.1021/acscatal.7b02117

upstream raw materials:

tert-Butyl 4-nitrophenyl carbonate

L-proline

carbon dioxide

tert-butyl pyrrolidine-1-carboxylate

Downstream raw materials:

tert-butyl (S)-2-(pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate

(S)-N-(tert-butoxycarbonyl)proline methyl ester

tert-butyl (S)-2-(diazoacetyl)pyrrolidine-1-carboxylate

(S)-1-methyl-2-(piperidinomethyl)pyrrolidine

Refernces

• 1、 Bayer,E. et al.. "-". . p. 4853 - 4860. Retrieved 1968.
• 2、 Sun, Ying,Bai, Yujun,He, Xirui,Bai, Yajun,Liu, Pei,Zhao, Zefeng,Chen, Xufei,Zheng, Xiaohui. "Design, synthesis and evaluation of novel 2-hydroxypyrrolobenzodiazepine-5, 11-dione analogues as potent angiotensin converting enzyme (ACE) inhibitors". . . Retrieved 2017.
• 3、 Nicola, A. De,Einhorn, C.,Einhorn, J.,Luche, J. L.. "Intramolecular Alkylation of Carboxylic Acids: Application to the Synthesis of Boc-Protected Cyclic Amino Acids". . p. 879 - 880. Retrieved 1994.
• 4、 Renard, C,Michel, A.,Tulkens, P. M.. "Hydrolysis of Pro-Ala Dipeptides by Lysosomal Hydrolases. Models for the Study of Lysosomotropic Amino Acid Prodrugs of Penicillins". . p. 1291 - 1293. Retrieved 1986.
• 5、 Georgiou, Irene,Whiting, Andrew. "Enantioselective synthesis of (R)-homoboroproline from (S)-proline using a borylation approach". . p. 4110 - 4113. Retrieved 2012.
• 6、 Li, Chonglong,Wang, Jihai,Ding, Huiyun. "Recyclable Helical Poly(phenyl isocyanide)-Supported l-Proline Catalyst for Direct Asymmetric Aldol Reaction in Brine". . p. 1180 - 1190. Retrieved 2020/09/07.
• 7、 Du, Yihao,Erdem, Safiye S.,Sari, Ozlem,Whiting, Andrew. "A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State". . . Retrieved 2021/11/17.