177530-93-7

Basic information

• Product Name: L 741211
• Synonyms: 2H-3,1-Benzoxazin-2-one, 6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-;L 741211;6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-3-one;Efavirenz Racemic (20 mg) ((+/-)-6-Chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one);rac Efavirenz
• CAS NO: 177530-93-7
• Molecular Formula: C₁₄H₉ClF₃NO₂
• Molecular Weight: 315.67
• Mol File: 177530-93-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Acetone (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: L 741211(CAS DataBase Reference)
• NIST Chemistry Reference: L 741211(177530-93-7)
• EPA Substance Registry System: L 741211(177530-93-7)

Safety Data

• Hazardous Substances Data: 177530-93-7(Hazardous Substances Data)

Usage

Uses

rac Efavirenz is a mixture of both enantiomers for Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor. Antiviral.

Upstream product

• 201218-10-2 4-cyclopropyl-1,1,1-trifluoro-but-3-yn-2-one 
• 50893-53-3 carbonochloridic acid 1-chloro-ethyl ester 
• 1262030-21-6 N-(4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl)acetamide 
• 1381993-87-8 4-cyclopropyl-2-(2,5-dichlorophenyl)-1,1,1-trifluorobut-3-yn-2-ol 
• 886371-22-8 1-(2,5-dichloro-phenyl)-2,2,2-trifluoroethanone 
• 1381993-89-0 carbamic acid cyclopropyl-(2,5-dichloro-phenyl)-trifluoromethyl-prop-2-ynyl ester 
• 106-46-7 para-dichlorobenzene 
• 2621-80-9 ethyl p-chlorophenylcarbamate 
• 201218-07-7 tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate 
• 6746-94-7 Cyclopropylacetylene 
• 201218-08-8 tert-butyl 4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenylcarbamate 
• 181190-33-0 N-(4-chloro-2-(2,2,2-trifluoroacetyl)phenyl)pivalamide 
• 154598-53-5 1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 154801-74-8 (R)-efavirenz 
• 154598-52-4 efavirenz 

Relevant articles and documents

PROCESS FOR PREPARING EFAVIRENZ

The invention disclosed a 4 step process for the preparation of Efavirenz, starting from 1,4-dichlorobenzene, and its intermediates.

PROCESS FOR PREPARATION OF EFAVIRENZ BY CYCLISATION

The invention disclosed a process for the preparation of the HIV drug Efavirenz, also known as DMP-266, starting from 1,4-dichlorobenzene, and its intermediates.

New synthetic technologies for the construction of heterocycles and tryptamines

New synthetic methods for the construction of novel heterocycles and tryptamines are described. Thus, N-Boc anilines (I) are sequentially converted to heterocycles II ((3-(2-aminophenyl)pyrrolidin-3-ol) derivatives),III (substituted 2-oxo-1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrol idines), and VI (2-(4,5-dihydro-1H-pyrrol-3-yl)aniline) derivatives through a route involving t-BuLi induced ortho-metalation/ LaCl3 2LiCl metalexchange, reaction with N-Boc pyrrolidin-3-one (5), and subsequent deca rboxylative fragmentation. Labile intermediates VI are effectively converted to tryptamines Xa and Xb under controlled proticacidconditions.Inadditiontoprovidingexpedientaccesstothe2-oxo- 1,2-dihydrospirobenzo[d][1,3]oxazine-4,3'-pyrrolidines (III), the method is applicable to the synthesis of the corresponding 2-oxo-1,2-dihydrospirobenzo[d] [1,3]oxazine-4,3'-piperidine series of spirocycles (e.g., 42) and their precursors (3-(2-aminophenyl)piperidin-3-ol derivatives, e.g., 43) by using N-Boc-protected piperidin-3-one (40). Applications of the developed synthetic technologies to the synthesis of regioisomeric spirocycles 87 and 90, tryptamines 88 and 91, Corey's aspidophytine tryptamine (97), and efavirenz (1) are also described.