474021-97-1

Basic information

• Product Name: (S)-N-(3-Bromo-2-acetoxypropyl)acetamide
• Synonyms: (S)-N-Acetoxy-3-bromo-2-acetoxyproylamine;(S)-N-(3-BROMO-2-ACETOXYPROPYL)ACETAMIDE;(S)-N-Acetoxy-3-bromo-2-acetoxypropylamine
• CAS NO: 474021-97-1
• Molecular Formula: C₇H₁₂BrNO₃
• Molecular Weight: 238.08
• Mol File: 474021-97-1.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 387.1°C at 760 mmHg
• Flash Point: 187.9°C
• Appearance: /
• Density: 1.425g/cm³
• Vapor Pressure: 3.38E-06mmHg at 25°C
• Refractive Index: 1.481
• PKA: 15.37±0.46(Predicted)
• CAS DataBase Reference: (S)-N-(3-Bromo-2-acetoxypropyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-(3-Bromo-2-acetoxypropyl)acetamide(474021-97-1)
• EPA Substance Registry System: (S)-N-(3-Bromo-2-acetoxypropyl)acetamide(474021-97-1)

Safety Data

• Hazardous Substances Data: 474021-97-1(Hazardous Substances Data)

Usage

General Description

(S)-N-(3-Bromo-2-acetoxypropyl)acetamide is a chemical compound with the molecular formula C6H10BrNO3. The compound is made up of a bromine atom, two acetoxypropyl groups, and an acetamide group. It is a derivative of acetamide and has a chiral center, giving it a specific stereochemistry. (S)-N-(3-Bromo-2-acetoxypropyl)acetamide may have potential applications in organic synthesis, pharmaceuticals, and biomedical research due to its unique structural features and potential reactivity. Its properties and potential uses may be further investigated in scientific studies.

InChI:InChI=1/C7H12BrNO3/c1-5(10)9-4-7(3-8)12-6(2)11/h7H,3-4H2,1-2H3,(H,9,10)/t7-/m1/s1

Synthetic route

(S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide (474021-97-1) → N-[(2S)oxiranylmethyl]acetamide (183805-10-9)

Conditions	Yield
With potassium carbonate In methanol; acetonitrile at 0 - 20℃;	90%
With potassium carbonate In methanol; acetonitrile at 0 - 20℃;	90%
With potassium carbonate In methanol; acetonitrile at 0 - 20℃;	90%
With potassium carbonate In methanol; acetonitrile at 0 - 20℃;	90%

(S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide (474021-97-1) + 3,5-difluoro-4-[3-(tetrazol-2-yl-pyrrolidin-1-yl)]-phenyl carbamic acid benzyl ester (1203468-38-5) → N-((5S)-3-{3,5-difluoro-4-[3-(tetrazol-2-yl)pyrrolidin-1-yl]-phenyl}-2-oxo-5-oxazolidinylmethyl)acetamide (1203468-33-0)

Conditions	Yield
Stage #1: 3,5-difluoro-4-[3-(tetrazol-2-yl-pyrrolidin-1-yl)]-phenyl carbamic acid benzyl ester With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 20℃; for 48h;	86%

isobutyl 4-(1,1-dioxidothiomorpholin-4-yl)-3,5-difluorophenylcarbamate (473871-38-4) + (S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide (474021-97-1) → PNU-288034

Conditions	Yield
With lithium tert-butoxide In tetrahydrofuran; methanol; acetonitrile	83%

(S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide (474021-97-1) + 3-Fluoro-4-(3-cyanopyrrolidin-1-yl)phenylcarbamic acid benzyl ester (1202878-56-5) → N-{(5S)-3-[3-fluoro-4-(3-cyanopyrrolidin-1-yl)phenyl]-2-oxo-5-oxazolidinylmethyl}acetamide (1202878-52-1)

Conditions	Yield
Stage #1: 3-Fluoro-4-(3-cyanopyrrolidin-1-yl)phenylcarbamic acid benzyl ester With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 20℃; for 96h;	63%

(S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide (474021-97-1) + benzyl [4-(4-cyano-piperidin-1-yl)-3-fluoro-phenyl]-carbamate (1161781-97-0) → (S)-N-{3-[4-(4-cyano-piperidin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (928160-67-2)

Conditions	Yield
Stage #1: benzyl [4-(4-cyano-piperidin-1-yl)-3-fluoro-phenyl]-carbamate With lithium tert-butoxide In methanol; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide In methanol; N,N-dimethyl-formamide at 20℃; for 48h; Product distribution / selectivity;	59%

(S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide (474021-97-1) + benzyl 3-fluoro-4-(1-methyl-1H-tetrazole-5yl)-phenyl carbamate → N-[[(5S)-3-[3-fluoro-4-(1-methyl-1H-tetrazol-5-yl)-phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (1161795-23-8)

Conditions	Yield
Stage #1: benzyl 3-fluoro-4-(1-methyl-1H-tetrazole-5yl)-phenyl carbamate With lithium tert-butoxide In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: (S)-N-[2-(acetyloxy)-3-bromopropyl]acetamide In tetrahydrofuran; methanol; N,N-dimethyl-formamide at 20℃; for 96h; Product distribution / selectivity;

Downstream Products

• 383199-88-0 PNU-288034 
• 928160-67-2 (S)-N-{3-[4-(4-cyano-piperidin-1-yl)-3-fluoro-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide 
• 183805-10-9 N-[(2S)oxiranylmethyl]acetamide 
• 1203468-33-0 N-((5S)-3-{3,5-difluoro-4-[3-(tetrazol-2-yl)pyrrolidin-1-yl]-phenyl}-2-oxo-5-oxazolidinylmethyl)acetamide 
• 1202878-52-1 N-{(5S)-3-[3-fluoro-4-(3-cyanopyrrolidin-1-yl)phenyl]-2-oxo-5-oxazolidinylmethyl}acetamide