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

Base Information

• Chemical Name: (2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
• CAS No.: 132622-66-3
• Molecular Formula: C10H18N2O4
• Molecular Weight: 230.264
• European Community (EC) Number: 800-921-5
• DSSTox Substance ID: DTXSID70564609
• Nikkaji Number: J1.830.368J
• Mol file: 132622-66-3.mol

Synonyms:132622-66-3;cis-1-Boc-4-Amino-L-proline;(2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;(2S,4S)-1-Boc-4-Aminopyrrolidine-2-carboxylic acid;(2S,4S)-1-BOC-4-AMINO-PYRROLIDINE-2-CARBOXYLIC ACID;MFCD03427029;(2S,4S)-4-amino-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid;(2S,4S)-4-AMINO-1,2-PYRROLIDINEDICARBOXYLIC ACID 1-(1,1-DIMETHYLETHYL) ESTER;1,2-PYRROLIDINEDICARBOXYLIC ACID, 4-AMINO-, 1-(1,1-DIMETHYLETHYL) ESTER, (2S,4S)-;(2S,4S)-4-AMINO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;cis-4-Amino-1-Boc-2-pyrrolidinecarboxylic acid;boc-(2s,4s)-4-aminoproline;SCHEMBL2708304;(2S,4S)-4-Amino-1-tert-butoxycarbonyl-pyrrolidine-2-carboxylic acid;DTXSID70564609;WDWRIVZIPSHUOR-BQBZGAKWSA-N;AMY36423;(2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylicacid;AKOS005264518;AKOS015841259;CS-W003074;AS-19526;A2800;EN300-82613;(4S)-1-(tert-Butoxycarbonyl)-4-amino-L-proline;(4S)-4-Amino-1-(tert-butoxycarbonyl)-L-proline;(2S,4S)-(1-Boc)-4-Amino-pyrrolidine-2-carboxylic acid;(2S,4S)-4-AMINO-1-(TERTBUTOXYCARBONYL)CARBOXYLIC ACID;(2S,4S)-4-AMINO-1-BOC-PYRROLIDINE-2-CARBOXYLIC ACID;(2S,4S)-4-Amino-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid;(2S,4S)-4-amino-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

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

Chemical Property:

• Vapor Pressure: 1.59E-06mmHg at 25°C
• Melting Point: >266 °C(lit.)
• Refractive Index: 1.516
• Boiling Point: 371.1 °C at 760 mmHg
• PKA: 3.65±0.20(Predicted)
• Flash Point: 178.2 °C
• PSA: 92.86000
• Density: 1.232g/cm³
• LogP: 1.04590
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 230.12665706
• Heavy Atom Count: 16
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

(2S,4S)-4-Amino-1,2-pyrrolidinedicarboxylicAcid1-(1,1-Dimethylethyl)Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)N
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@H](C[C@H]1C(=O)O)N
• Uses: also available as trans isomer, see 1-00971

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

There total 15 articles about (2S,4S)-4-amino-1-(tert-butoxycarbonyl)pyrrolidine-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: 100.0%

(2S,4S)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate (874162-96-6) → cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline (132622-66-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 24h;

DOI:10.1021/jm701214z

Reference yield: 84.0%

azido acid + (4S)-1-(tert-butoxycarbonyl)-4-azido-L-proline (132622-65-2) → cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline (132622-66-3)

Guidance literature:

palladium-carbon; In ethanol; water;

Reference yield: 84.0%

(4S)-1-(tert-butoxycarbonyl)-4-azido-L-proline (132622-65-2) → cis-1-(1,1-dimethylethyoxycarbonyl)-4-amino-L-proline (132622-66-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; for 16h; under 5171.5 Torr;

DOI:10.1021/jo00009a016

upstream raw materials:

(4S)-1-(tert-butoxycarbonyl)-4-azido-L-proline

(2S,4S)-4-aminopyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester hydrochloride

(2S,4S)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate

2-benzyl 1-(tert-butyl) (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate

Downstream raw materials:

(2S,4S)-4-(((benzyloxy)carbonyl)amino)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide

methyl 3(R)-[(4(S)-(4-benzyloxycarbonylamino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetate

3(R)-[(4(S)-((4-azidobenzoyl)amino)-1-(tert-butoxycarbonyl)-2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide