165683-88-5

Basic information

• Product Name: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER
• Synonyms: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER;Carbamic acid, [(1S)-1-(2S)-oxiranylethyl]-, 1,1-dimethylethyl ester (9CI)
• CAS NO: 165683-88-5
• Molecular Formula: C₉H₁₇NO₃
• Molecular Weight: 187.24
• Product Categories: N-BOC
• Mol File: 165683-88-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 48-50 °C(Solv: dichloromethane (75-09-2); pentane (109-66-0))
• Boiling Point: 272.6±13.0 °C(Predicted)
• Appearance: /
• Density: 1.071±0.06 g/cm3(Predicted)
• PKA: 12.23±0.46(Predicted)
• CAS DataBase Reference: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER(165683-88-5)
• EPA Substance Registry System: [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER(165683-88-5)

Safety Data

• Hazardous Substances Data: 165683-88-5(Hazardous Substances Data)

Usage

Description

[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER, with the molecular formula C10H19NO3, is a tert-butyl ester derivative of a carbamic acid. It is a compound that serves as a crucial chiral building block in the synthesis of pharmaceuticals and agrochemical products. This versatile chemical is produced through the reaction of tert-butyl carbamate and epichlorohydrin, and it is known for its various properties and applications in organic synthesis and medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER is used as a chiral building block for the development of pharmaceutical compounds. Its unique structure allows for the creation of new drugs with improved efficacy and selectivity, contributing to advancements in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical industry, [1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER is utilized as a key intermediate in the synthesis of various agrochemical products. Its incorporation aids in the development of more effective and targeted pesticides, herbicides, and other agricultural chemicals.
Used in Organic Synthesis:
[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER is also used as a valuable intermediate in organic synthesis, allowing for the creation of a wide range of organic molecules with diverse applications. Its versatility and reactivity make it an important building block in the field of organic chemistry.
Used in Medicinal Chemistry:
[1(S)-METHYL-2(S),3-EPOXYPROPYL]-CARBAMIC ACID TERT-BUTYL ESTER plays a significant role in medicinal chemistry, where it is employed in the design and synthesis of novel therapeutic agents. Its unique properties enable the development of drugs with improved pharmacological profiles and targeted action against specific diseases.

Upstream product

• 154079-54-6 (2S,3S)-3-tert-butoxycarbonylamino-1,2-butanediol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 178421-71-1 (2S,3S)-3-tert-butoxycarbonylamino-1-tosyloxy-2-butanol 
• 545375-08-4 ((1S,2S)-3-Chloro-2-hydroxy-1-methyl-propyl)-carbamic acid tert-butyl ester 
• 51814-53-0 N-tert-butoxycarbonyl-L-alanine ethyl ester 
• 93371-30-3 tert-butyl [(2S)-4-chloro-3-oxobutan-2-yl]carbamate 

Relevant articles and documents

Stereoselective synthesis of anti-N-protected 3-amino-1,2-epoxides by nucleophilic addition to N-tert-butanesulfinyl imine of a glyceraldehyde synthon

(Chemical Equation Presented) A di-O-TBS protected glyceraldehyde synthon was condensed with Ellman's reagent to form a bench-stable N-tert-butanesulfinyl imine 6, which served as a common intermediate for the stereoselective introduction of various R groups. The Ellman adducts were converted to useful multifunctional intermediates 18a-i in one pot. The alcohols 18a-i were efficiently elaborated to both known and novel anti-N-protected-3-amino-1,2- epoxides in two steps. Compound 2a is a key intermediate toward HIV protease inhibitors.

Synthesis and γ-secretase activity of APP substrate-based hydroxyethylene dipeptide isosteres

Two new APP substrate-based hydroxyethylene isosteres (AT and VI) were prepared and their dipeptide conjugates shown not to inhibit the γ-secretase-mediated formation of either Aβ1-40 or Aβ1-42. The FG isostere and a des-hydroxy hydroxyethylene isostere a

Preparation of aminoalkyl chlorohydrin hydrochlorides: Key building blocks for hydroxyethylamine-based HIV protease inhibitors

Enantiomerically pure N,N-dibenzyl-α-amino aldehydes reacted with (chloromethyl)lithium, generated in situ from bromochloromethane and lithium metal, to give predominantly erythro aminoalkyl epoxides. Treatment of the crude epoxides with aqueous hydrochloric acid gave crystalline (2S,3S)-N,N-dibenzylamino chlorohydrin hydrochlorides in 32-56% overall yield and high isomeric purity. These compounds are versatile synthetic intermediates for the preparation of hydroxyethylamine-based HIV protease inhibitors, either directly as such, or via conversion to the corresponding N-Boc(2S,3S)-aminoalkyl epoxides. The processes described do not make use of hazardous reagents or intermediates, do not require chromatographic purifications, and are thus amenable to the preparation of large quantities of these versatile building blocks.