Efavirenz amino alcohol methyl carbamate

Base Information

• Chemical Name: Efavirenz amino alcohol methyl carbamate
• CAS No.: 211563-40-5
• Molecular Formula: C15H13 Cl F3 N O3
• Molecular Weight: 347.721
• UNII: 376R1A850V
• Nikkaji Number: J1.067.510C
• Wikidata: Q27256642
• Mol file: 211563-40-5.mol

Synonyms:211563-40-5;Efavirenz amino alcohol methyl carbamate;SD 573 methyl carbamate;SV-993;376R1A850V;[4-Chloro-2-[(1S)-3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propynyl)phenyl]carbamic Acid Methyl Ester;UNII-376R1A850V;methyl N-[4-chloro-2-[(2S)-4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl]phenyl]carbamate;[4-Chloro-2-[(1S)-3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propynyl)phenyl]carbamic Acid Methyl;Methyl [4-Chloro-2-((1S)-1-trifluoromethyl-1-hydroxy-3-cyclopropyl-2-propyn-1-yl)phenyl]carbamate;METHYL (4-CHLORO-2-((1S)-1-TRIFLUOROMETHYL-1-HYDROXY-3-CYCLOPROPYL-2-PROPYN-1-YL)PHENYL)CARBAMATE;EFAVIRENZ IMPURITY I [WHO-IP];A899518;J-013888;Q27256642;EFAVIRENZ AMINO ALCOHOL METHYL CARBAMATE [USP IMPURITY];EFAVIRENZ IMPURITY, EFAVIRENZ AMINO ALCOHOL METHYL CARBAMATE-;(S)-METHYL 4-CHLORO-2-(4-CYCLOPROPYL-1,1,1-TRIFLUORO-2-HYDROXYBUT-3-YN-2-YL)PHENYLCARBAMATE;CARBAMIC ACID, (4-CHLORO-2-((1S)-3-CYCLOPROPYL-1-HYDROXY-1-(TRIFLUOROMETHYL)-2-PROPYNYL)PHENYL)-, METHYL ESTER;CARBAMIC ACID, N-(4-CHLORO-2-((1S)-3-CYCLOPROPYL-1-HYDROXY-1-(TRIFLUOROMETHYL)-2-PROPYN-1-YL)PHENYL)-, METHYL ESTER

Chemical Property of Efavirenz amino alcohol methyl carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.58
• Boiling Point: 427.446°C at 760 mmHg
• PKA: 9.21±0.24(Predicted)
• Flash Point: 212.312°C
• PSA: 58.56000
• Density: 1.56g/cm³
• LogP: 3.75460
• Solubility.: Chloroform, Dichloromethane, Dimethyl Sulfoxide, Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 347.0536055
• Heavy Atom Count: 23
• Complexity: 523

Purity/Quality:

97% ^*data from raw suppliers

[4-Chloro-2-[(1S)-3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propynyl)phenyl]carbamicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)NC1=C(C=C(C=C1)Cl)C(C#CC2CC2)(C(F)(F)F)O
• Isomeric SMILES: COC(=O)NC1=C(C=C(C=C1)Cl)[C@@](C#CC2CC2)(C(F)(F)F)O

Technology Process of Efavirenz amino alcohol methyl carbamate

There total 2 articles about Efavirenz amino alcohol methyl 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: 92.0%

methyl chloroformate (79-22-1) + (2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol (209414-27-7,927812-33-7,154598-58-0) → [4-Chloro-2-((S)-3-cyclopropyl-1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-carbamic acid methyl ester (211563-40-5)

Guidance literature:

With potassium hydrogencarbonate; In water; toluene; at 20 - 25 ℃; for 8.5h;

DOI:10.1021/jo981170l

Reference yield:

(S)-6-chloro-4-(cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine (209414-26-6) → [4-Chloro-2-((S)-3-cyclopropyl-1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-carbamic acid methyl ester (211563-40-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaOH, 2.) NaOH, NaBH₄ / 1.) methanol, toluene, 40 deg C, 30 min, 2.) methanol, toluene, room temperature, 15 min

2: 92 percent / potassium bicarbonate / toluene; H₂O / 8.5 h / 20 - 25 °C

With sodium hydroxide; sodium tetrahydroborate; potassium hydrogencarbonate; In water; toluene;

DOI:10.1021/jo981170l

Reference yield: 96.0%

[4-Chloro-2-((S)-3-cyclopropyl-1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-carbamic acid methyl ester (211563-40-5) → efavirenz (154598-52-4,154635-17-3)

Guidance literature:

[4-Chloro-2-((S)-3-cyclopropyl-1-hydroxy-1-trifluoromethyl-prop-2-ynyl)-phenyl]-carbamic acid methyl ester; With lithium tert-butoxide; In methyl t-butyl ether (MTBE); at 20 - 25 ℃; for 16h;

With hydrogenchloride; In methyl t-butyl ether (MTBE); water; Product distribution / selectivity;

upstream raw materials:

methyl chloroformate

(2S)-2-(2-amino-5-chlorophenyl)-4-cyclopropyl-1,1,1-trifluorobut-3-yn-2-ol

(S)-6-chloro-4-(cyclopropylethynyl)-2-(4-methoxyphenyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazine

Downstream raw materials:

efavirenz