(2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid
• CAS No.: 147266-79-3
• Molecular Formula: C16H21 N O5
• Molecular Weight: 307.346
• Hs Code.: 29339900
• European Community (EC) Number: 865-460-4
• Mol file: 147266-79-3.mol

Synonyms:147266-79-3;(2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid;(2S,4S)-1-(TERT-BUTOXYCARBONYL)-4-PHENOXY-2-PYRROLIDINECARBOXYLIC ACID;N-BOC-cis-4-Phenoxy-L-proline;(2S,4S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenoxypyrrolidine-2-carboxylic acid;(2S,4S)-1-[(Tert-Butoxy)Carbonyl]-4-Phenoxypyrrolidine-2-Carboxylic Acid;(2S,4S)-boc-4-Phenoxy-pyrrolidine-2-carboxylic acid;(4S)-N-Boc-4-phenoxy-L-proline;(2S,4S)-Boc-4-phenoxy-Pro-OH;SCHEMBL252870;MFCD06656447;AKOS005265029;AKOS015838350;AS-72649;C72805;EN300-6473637;A884443;(2S, 4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid;(2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxy-pyrrolidine-2-carboxylic acid;(2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylicacid;(2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid

Chemical Property of (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 4.24E-09mmHg at 25°C
• Boiling Point: 455.8°Cat760mmHg
• PKA: 3.66±0.40(Predicted)
• Flash Point: 229.4°C
• PSA: 76.07000
• Density: 1.235g/cm³
• LogP: 2.46590
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 307.14197277
• Heavy Atom Count: 22
• Complexity: 411

Purity/Quality:

98.5% ^*data from raw suppliers

(2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxy-2-pyrrolidinecarboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)OC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)OC2=CC=CC=C2

Technology Process of (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid

There total 5 articles about (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic 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: 92.0%

N-Boc-cis-4-phenoxy-L-proline benzyl ester (221050-87-9) → (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid (147266-79-3,158459-12-2,2380783-50-4,147267-15-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2008.10.120

Reference yield: 58.0%

methyl (1-tert-butoxycarbonyl)-(4S)-phenoxy-(2S)-pyrrolidinylcarboxylate (93967-75-0) → (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid (147266-79-3,158459-12-2,2380783-50-4,147267-15-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2005.11.058

Reference yield:

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (74844-91-0) → (2S,4S)-1-(tert-butoxycarbonyl)-4-phenoxypyrrolidine-2-carboxylic acid (147266-79-3,158459-12-2,2380783-50-4,147267-15-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / diisopropyl azodicarboxylate; PPh₃ / tetrahydrofuran / 12 h / 20 °C

2: 58 percent / aq. NaOH / tetrahydrofuran / 12 h / 20 °C

With sodium hydroxide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 1: Mitsunobu reaction;

DOI:10.1016/j.bmc.2005.11.058

upstream raw materials:

methyl (1-tert-butoxycarbonyl)-(4S)-phenoxy-(2S)-pyrrolidinylcarboxylate

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

phenol

N-Boc-cis-4-phenoxy-L-proline benzyl ester

Downstream raw materials:

N-1-Boc-cis-4-phenoxy-L-(2-hydroxyphenyl)pyrrolidine-2-carboxamide

N-1-Boc-cis-4-phenoxy-L-(5-methyl-2-hydroxyphenyl)pyrrolidine-2-carboxamide

N-1-Boc-cis-4-phenoxy-L-(5-tert-butyl-2-hydroxyphenyl)pyrrolidine-2-carboxamide

(2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidine carbaldehyde

Refernces

• 1、 Chiba, Jun,Takayama, Gensuke,Takashi, Tohru,Yokoyama, Mika,Nakayama, Atsushi,Baldwin, John J.,McDonald, Edward,Moriarty, Kevin J.,Sarko, Christopher R.,Saionz, Kurt W.,Swanson, Robert,Hussain, Zahid,Wong, Angela,MacHinaga, Nobuo. "Synthesis, biological evaluation, and pharmacokinetic study of prolyl-1-piperazinylacetic acid and prolyl-4-piperidinylacetic acid derivatives as VLA-4 antagonists". . p. 2725 - 2746. Retrieved 2007/10/03.
• 2、 -. "VLA-4 INHIBITORS". . . Retrieved 2008/06/13.