67706-68-7

Basic information

• Product Name: TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE
• Synonyms: TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE;Ethyl 4-((tert-butoxycarbonyl)aMino)-3-oxobutanoate;4-(Boc-amino)-3-oxobutanoic acid ethyl ester
• CAS NO: 67706-68-7
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.28
• Mol File: 67706-68-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE(67706-68-7)
• EPA Substance Registry System: TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE(67706-68-7)

Safety Data

• Hazardous Substances Data: 67706-68-7(Hazardous Substances Data)

Usage

General Description

TERT-BUTYL 3-(ETHOXYCARBONYL)-2-OXOPROPYLCARBAMATE is a chemical compound that features in the production of several pharmaceuticals. It has roles in the chemical industry as a protecting group for amines in synthesis processes, mainly due to its stability and the ease of its removal following synthesis. The compound consists of a carbamate group (-NHCOO-) and a tert-butyl group, with an ethoxycarbonyl functional group attached. It is an organic substance and can be manipulated using different catalysts or under varied environmental conditions for diverse manufacturing purposes. Despite its widespread use, its inhalation, ingestion or contact with eyes or skin may be harmful.

Upstream product

• 4530-20-5 BOC-glycine 
• 35116-15-5 Dibasic magnesium salt of ethyl hydrogen malonate 
• 1071-46-1 hydrogen ethyl malonate 
• 18185-77-8 tert-butyloxycarbonylglycine imidazolide 
• 6148-64-7 ethyl potassium malonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 86578-55-4 4-azidoacetoacetic acid ethyl ester 
• 66866-43-1 N-(t-butoxycarbonyl)glycyl i-butyl carbonate 
• 141-78-6 ethyl acetate 

Downstream Products

• 1341195-70-7 1-[(tert-butoxycarbonyl)amino]-4-ethoxy-4-oxobutan-2-yl 4-nitrobenzoate 
• 835873-55-7 4-tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-but-2-enoic acid ethyl ester 
• 835873-54-6 4-tert-butoxycarbonylamino-3-(toluene-4-sulfonyloxy)-but-2-enoic acid ethyl ester 

Relevant articles and documents

Access to dihydropyrano[3,2-: B] pyrrol-5-ones skeletons by N-heterocyclic carbene-catalyzed [3+3] annulations

A novel and efficient NHC-catalyzed [3+3] annulation of enals with pyrrol-4-ones was developed, thus providing the dihydropyrano[3,2-b]pyrrol-5-one core structures with broad scope and good to excellent enantioselectivities. Notably, this strategy could also expand to the synthesis of axially chiral compounds and polysubstituted indoles.

Ru-catalyzed asymmetric hydrogenation of γ-heteroatom substituted β-keto esters

A series of enantiomerically pure γ-heteroatom substituted β-hydroxy esters were synthesized with high enantioselectivities (up to 99.1% ee) by hydrogenation of γ-heteroatom substituted β-keto esters in the presence of Ru-(S)-SunPhos catalyst. These asymmetric hydrogenations provide key building blocks for a variety of naturally occurring and biologically active compounds.

A convergent route for the total synthesis of malyngamides O, P, Q, and R

(Chemical Equation Presented) A convergent, enantioselective and general synthetic route to a class of marine natural products - malyngamides O (1), P (2), Q (3), R (4), 5″-epi-3 and 5″-epi-4 - bearing a novel vinyl chloride structural motif was developed. The key steps involved construction of the vinyl chloride functionality by Wittig reaction, a DCC/HOBt-promoted amidation, an aldol reaction in the construction of the basic backbone of 1, 2, 3, 4, 5″-epi-3, and 5″-epi-4, and methylation of an enol moiety via either base/acid conditions or a Mitsunobu reaction. Moreover, the absolute configuration of the stereogenic center at C-5″ in 3 was further confirmed by synthesis of the natural product and its C-5″ epimer.