tert-butyl N-[1-(oxiran-2-yl)-2-phenylethyl]carbamate

Base Information

• Chemical Name: tert-butyl N-[1-(oxiran-2-yl)-2-phenylethyl]carbamate
• CAS No.: 98737-29-2
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.337
• Hs Code.: 29242990
• European Community (EC) Number: 619-373-1,425-420-5
• DSSTox Substance ID: DTXSID70869323
• Mol file: 98737-29-2.mol

Synonyms:tert-butyl N-[1-(oxiran-2-yl)-2-phenylethyl]carbamate;103127-56-6;98737-29-2;(2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane;threo-N-Boc-L-phenylalanine epoxide;MFCD00671705;MFCD02258997;tert-butyl 1-(oxiran-2-yl)-2-phenylethylcarbamate;TERT-BUTYL[(1S,2R)-OXIRANYL-2-PHENYLETHYL]CARBAMATE;SCHEMBL2079109;DTXSID70869323;(chlorophthalocyaninato)copper(ii);NVPOUMXZERMIJK-UHFFFAOYSA-N;Tert-butyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-phenyl-ethyl]carbamate;AKOS025243924;SB46310;SB46651;LS-14425;SY014396;SY014525;FT-0604672;FT-0642378;FT-0663441;FT-0730998;NS00003001;EN300-295798;tert-butyl-(1-oxiranyl-2-phenylethyl)-carbamate;tert-Butyl 1-(2-oxiranyl)-2-phenylethylcarbamate;tert-Butyl [1-(oxiran-2-yl)-2-phenylethyl]carbamate;tert-butylN-[1-(oxiran-2-yl)-2-phenylethyl]carbamate;(1-Oxiranyl-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Chemical Property of tert-butyl N-[1-(oxiran-2-yl)-2-phenylethyl]carbamate

Chemical Property:

• Appearance/Colour: off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 125-127 °C(lit.)
• Refractive Index: 1.533
• Boiling Point: 398.837 °C at 760 mmHg
• PKA: 12.19±0.46(Predicted)
• Flash Point: 195.01 °C
• PSA: 50.86000
• Density: 1.118 1.118 g/cm^>3
• LogP: 2.91210
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility.: Insoluble in water. Soluble in Chloroform, Dichloromethane and Ethyl Acetate.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 263.15214353
• Heavy Atom Count: 19
• Complexity: 305

Purity/Quality:

99% ^*data from raw suppliers

(2S,3S)-3-Boc-amino-1,2-epoxy-4-phenylbutane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi,N
• Statements: 10-36/37/38-50/53
• Safety Statements: 7/9-16-26-36/37/39-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C2CO2
• Uses: It function as a building block employed in the synthesis of HIV-1 protease inhibitors and is also employed in synthesizing (hydroxyethyl)urea peptidomimetrics and arylsulfonamides possessing anti-HIV activity. It is a Enantiomer S. Atazanavir intermediate.

Technology Process of tert-butyl N-[1-(oxiran-2-yl)-2-phenylethyl]carbamate

There total 188 articles about tert-butyl N-[1-(oxiran-2-yl)-2-phenylethyl]carbamate 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: 98.0%

(2S,3S)-3-(tert-butoxycarbonyl)amino-4-phenyl-1-tosyloxy-2-butanol (149451-81-0) → (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2)

Guidance literature:

With potassium carbonate; In methanol; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2009.08.001

Reference yield: 93.0%

(2S,3S)-1-bromo-3-<(tert-butoxycarbonyl)amino>-4-phenyl-2-butanol (136630-87-0) → (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2)

Guidance literature:

With potassium hydroxide; In ethanol; for 1h; Ambient temperature;

DOI:10.1016/00404-0399(50)1087X-

Reference yield: 87.0%

isopropyl alcohol (67-63-0,8013-70-5) + tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate (165727-45-7) + citric acid (77-92-9,906507-37-7) → (1-oxiranyl-2-phenylethyl)carbamic acid tert-butyl ester (98760-08-8,98818-34-9,98818-35-0,103127-56-6,98737-29-2)

Guidance literature:

With sodium hydroxide; In water;

upstream raw materials:

methylenedimethyl sulfurane

Boc-L-phenylalaninal

((S)-1-benzylallyl)carbamic acid tert-butyl ester

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

Downstream raw materials:

[(1S,2R)-1-Benzyl-3-((S)-1-tert-butylcarbamoyl-2-phenyl-ethylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester

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

[R-(R*,S*)]-[3-Azido-2-hydroxy-1-(phenylmethyl) propyl]carbamic acid, 1,1-dimethylethyl ester

(1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester

Refernces

• 1、 Hu, Dianwen,Song, Xiaojing,Zhang, Hao,Chang, Xinyu,Zhao, Chen,Jia, Mingjun. "Aerobic epoxidation of styrene over Zr-based metal-organic framework encapsulated transition metal substituted phosphomolybdic acid". . . Retrieved 2021/04/19.
• 2、 Wang, Man,Liang, Gan,Wang, Yunhao,Fan, Tao,Yuan, Baoling,Liu, Mingxian,Yin, Ying,Li, Liangchun. "Merging N-Hydroxyphthalimide into Metal-Organic Frameworks for Highly Efficient and Environmentally Benign Aerobic Oxidation". supporting information. p. 9674 - 9685. Retrieved 2021/06/09.