Tert-butyl (2S)-2-aminopent-4-enoate

Base Information

• Chemical Name: Tert-butyl (2S)-2-aminopent-4-enoate
• CAS No.: 163210-82-0
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.239
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID60581603
• Nikkaji Number: J922.086K
• Mol file: 163210-82-0.mol

Synonyms:163210-82-0;(S)-2-AMINO-4-PENTENOIC ACID T-BUTYL ESTER;TERT-BUTYL (2S)-2-AMINOPENT-4-ENOATE;4-Pentenoic acid, 2-amino-, 1,1-dimethylethyl ester, (2S)-;DTXSID60581603;FFDXLHHMGNXXAG-ZETCQYMHSA-N;tert-butyl (S)-aminopent-4-enoate;(S)-tert-Butyl2-aminopent-4-enoate;AKOS015841390;EN300-7809780

Chemical Property of Tert-butyl (2S)-2-aminopent-4-enoate

Chemical Property:

• Vapor Pressure: 0.5±0.0 mmHg at 25°C
• Boiling Point: 193.5±0.0 °C at 760 mmHg
• Flash Point: 64.8±0.0 °C
• PSA: 52.32000
• Density: 1.0±0.0 g/cm3
• LogP: 1.93180
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 171.125928785
• Heavy Atom Count: 12
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-AMINO-4-PENTENOIC ACID-TERT-BUTYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(CC=C)N
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CC=C)N

Technology Process of Tert-butyl (2S)-2-aminopent-4-enoate

There total 11 articles about Tert-butyl (2S)-2-aminopent-4-enoate 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%

(S)-2-[(1S,4R)-1-(tert-Butylsulfamoyl-methyl)-7,7-dimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-pent-4-enoic acid tert-butyl ester → (S)-2-allylglycine tert-butyl ester (163210-82-0,199588-89-1)

Guidance literature:

With sodium hydroxide; hydroxylamine hydrochloride; acetic acid; In methanol; chloroform; at 25 ℃; for 24h;

DOI:10.1016/S0040-4020(97)00372-4

Reference yield: 89.0%

acetic acid tert-butyl ester (540-88-5) + (2S)-2-aminopent-4-enoic acid hydrochloride → (S)-2-allylglycine tert-butyl ester (163210-82-0,199588-89-1)

Guidance literature:

With perchloric acid; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/chem.202004004

Reference yield: 78.0%

tert-Butyl 2,2,2-trichloroacetimidate (98946-18-0) + 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid (146549-21-5) → (S)-2-allylglycine tert-butyl ester (163210-82-0,199588-89-1)

Guidance literature:

tert-Butyl 2,2,2-trichloroacetimidate; 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid; In dichloromethane; at 20 ℃; for 72h;

With diethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/acs.orglett.1c03532

upstream raw materials:

N-benzyloxy-L-allylglycine tert-butyl ester

N-(diphenylmethylene)glycine tert-butyl ester

allyl bromide

O-benzyl tert-butyl glyoxylate oxime ether

Downstream raw materials:

(S)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-aminopent-4-enehydroxamic acid

O-tert-butyl (S)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-aminopent-4-enehydroxamate

(S)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-aminopent-4-enoic acid

tert-butyl (S)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-aminopent-4-enoate

Refernces

• 1、 Engelhardt, Daniel B.,Pascoe, Cameron A.,Rosana, Albert Remus R.,Van Belkum, Marco J.,Vederas, John C.. "Methylene Analogues of Neopetrosiamide as Potential Antimetastatic Agents: Solid-Supported Syntheses Using Diamino Diacids for Pre-Stapling of Peptides with Multiple Disulfides". supporting information. p. 9216 - 9220. Retrieved 2021/11/30.
• 2、 Rull, Jordi,Jara, José Juan,Sebastián, Rosa M.,Vallribera, Adelina,Nájera, Carmen,Majoral, Jean-Pierre,Caminade, Anne-Marie. "Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts". . p. 2049 - 2056. Retrieved 2016/07/07.