(3S)-3-(Tert-butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone

Base Information

• Chemical Name: (3S)-3-(Tert-butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone
• CAS No.: 102123-74-0
• Molecular Formula: C15H20ClNO3
• Molecular Weight: 297.782
• Hs Code.: 2942000000
• UNII: UV1OR154Q5
• DSSTox Substance ID: DTXSID40432942
• Nikkaji Number: J835.952K
• Wikidata: Q72509722
• Mol file: 102123-74-0.mol

Synonyms:102123-74-0;(3S)-3-(TERT-BUTOXYCARBONYL)AMINO-1-CHLORO-4-PHENYL-2-BUTANONE;(S)-tert-Butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate;Boc-L-Phe chloromethyl ketone;(3S)-3-(N-Boc-amino)-1-chloro-4-phenyl-2-butanone;tert-butyl N-[(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate;UV1OR154Q5;tert-butyl (S)-(4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate;(3S)-(-)-3-tert-Butoxycarbonylamino-1-chloro-4-phenyl-2-butanone;Carbamic acid, N-((1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl)-, 1,1-dimethylethyl ester;Carbamic acid, N-[(1S)-3-chloro-2-oxo-1-(phenylmethyl)propyl]-, 1,1-dimethylethyl ester;UNII-UV1OR154Q5;SCHEMBL638877;DTXSID40432942;JAKDNFBATYIEIE-LBPRGKRZSA-N;AMY21566;BCP08425;CS-B0125;MFCD11041198;AKOS016842989;AC-8237;DS-14730;EN300-7407696;A800518;J-501274;Z1505699083;(3S)-1-chloro-3-tert-butoxycarbonylamino-4-phenyl-2-butanone;(3S)-3-tert-butoxycarbonylamino -1-chloro-4-phenyl-2-butanone;(3S)-3-tert-butoxycarbonylamino-1 -chloro-4-phenyl-2-butanone;(3S)-3-tert-butoxycarbonylamino-1-chloro -4-phenyl-2-butanone;(3S)-3-tert-butoxycarbonylamino-1-chloro-4-phenyl-2-butanone;(S)-1-Chloro-3-(tert-butoxycarbonylamino)-4-phenyl-2-butanone;(S)-tert-Butyl(4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate;[1(S)-benzyl-2-oxo-3-chloropropyl]carbamic acid t-butyl ester;tert-Butyl [(2S)-4-chloro-3-oxo-1-phenylbutan-2-yl]carbamate;tert-Butyl N-((1S)-1-Benzyl-3-chloro-2-oxopropyl)carbamate;N-(t-butoxycarbonyl)-(3s)-3-amino-1-chloro-4-phenyl-2-butanone;N-(tert-butyloxycarbonyl)-(3S)-3-amino-1-chloro-4-phenyl-2-butanone

Chemical Property of (3S)-3-(Tert-butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 103 °C
• Refractive Index: 1.517
• Boiling Point: 423.882 °C at 760 mmHg
• PKA: 10.94±0.46(Predicted)
• Flash Point: 210.157 °C
• PSA: 55.40000
• Density: 1.15 g/cm³
• LogP: 3.32120
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 297.1131712
• Heavy Atom Count: 20
• Complexity: 333

Purity/Quality:

99% ^*data from raw suppliers

(3S)-3-(tert-Butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)CCl
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)CCl

Technology Process of (3S)-3-(Tert-butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone

There total 23 articles about (3S)-3-(Tert-butoxycarbonyl)amino-1-chloro-4-phenyl-2-butanone 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%

(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate (60398-41-6) → (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (102123-74-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; diethyl ether; at 0 ℃; for 1h;

DOI:10.1021/jm00038a005

Reference yield: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (3S)-3-amino-1-chloro-4-phenyl-2-butanone hydrochloride (34351-19-4) → (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (102123-74-0) + 2,5-dibenzyl-3-chloromethyl-6-methyl-pyrazine

Guidance literature:

With sodium carbonate; In dichloromethane; water; at 35 ℃; for 1h;

DOI:10.1016/S0040-4039(01)01115-7

Reference yield: 89.0%

(S)-3-(tert-butoxycarbonyl)amino-4-phenyl-2-butanone (85613-64-5) → (S)-tert-butyl (4-chloro-3-oxo-1-phenylbutan-2-yl)carbamate (102123-74-0)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 20 ℃; for 2.5h;

upstream raw materials:

diazomethane

(C₅H₉O₂)C₉H₉NO(O)(CO₂C₂H₅)

(3S)-tert-butyl 1-benzyl-3-diazo-2-oxopropylcarbamate

Chloroiodomethane

Downstream raw materials:

Boc-Phe-4-acetylphenoxymethyl ketone

{(1S,2R)-1-Benzyl-3-[((S)-3-tert-butoxycarbonylamino-2-oxo-4-phenyl-butyl)-methyl-amino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester

tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate

(2R,3S)-1-Chloro-2-hydroxy-3-N-(tert-butoxycarbonyl)amino-4-phenylbutane

Refernces

• 1、 Chen, Ping,Cheng, Peter T. W.,Spergel, Steven H.,Zahler, Robert,Wang, Xuebao,Thottathil, John,Barrish, Joel C.,Polniaszek, Richard P.. "A practical method for the preparation of α'-chloroketones of N-carbanaate protected-α-aminoacids". . p. 3175 - 3178. Retrieved 1997.
• 2、 -. "Synthesis method of (2S, 3S)-3-(t-butyloxycarboryl amino)-1, 2-epoxy-4-phenylbutane". Paragraph 0043; 0046; 0049; 0052. . Retrieved 2021/06/23.
• 3、 -. "A process for the preparation method of the sulfuric acid [...] intermediates". Paragraph 0027; 0028. . Retrieved 2019/07/08.