(S)-2,2-dimethyl-1,3-dioxolane-4-acetamide

Base Information

• Chemical Name: (S)-2,2-dimethyl-1,3-dioxolane-4-acetamide
• CAS No.: 185996-33-2
• Molecular Formula: C₇H₁₃NO₃
• Molecular Weight: 159.185
• DSSTox Substance ID: DTXSID70370025
• Nikkaji Number: J3.276.677C
• Mol file: 185996-33-2.mol

Synonyms:185996-33-2;(S)-2,2-dimethyl-1,3-dioxolane-4-acetamide;2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetamide;ST50824729;SCHEMBL3376386;DTXSID70370025;PDKGYPMMTGPUCJ-YFKPBYRVSA-N;AKOS025401508;AC-20167;1,3-Dioxolane-4-acetamide,2,2-dimethyl-,(4S)-;(4s)-2,2-Dimethyl-1,3-dioxolane-4beta-acetamide;(S)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)acetamide

Chemical Property of (S)-2,2-dimethyl-1,3-dioxolane-4-acetamide

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.000683mmHg at 25°C
• Melting Point: 108-109 °C
• Refractive Index: 1.444
• Boiling Point: 308.4 °C at 760 mmHg
• Flash Point: 168.7 °C
• PSA: 61.55000
• Density: 1.078 g/cm³
• LogP: 0.71360
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 159.08954328
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2,2-DIMETHYL-1,3-DIOXOLANE-4-ACETAMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)CC(=O)N)C
• Isomeric SMILES: CC1(OC[C@@H](O1)CC(=O)N)C

Technology Process of (S)-2,2-dimethyl-1,3-dioxolane-4-acetamide

There total 2 articles about (S)-2,2-dimethyl-1,3-dioxolane-4-acetamide 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: 100.0%

2,2-dimethoxy-propane (77-76-9) + (S)-3,4-dihydroxybutyramide (126495-84-9) → (S)-4-(2,2-dimethyl)-1,3-dioxolane acetamide (185996-33-2)

Guidance literature:

2,2-dimethoxy-propane; (S)-3,4-dihydroxybutyramide; sulfuric acid; In acetone; at 20 - 60 ℃; for 12.5h;

With silver(l) oxide; In acetone; for 1h; Product distribution / selectivity;

Reference yield: 96.0%

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate (95422-24-5) → (S)-4-(2,2-dimethyl)-1,3-dioxolane acetamide (185996-33-2)

Guidance literature:

With ammonia; In water; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(96)02098-9

Reference yield: 86.0%

(S)-4-(2,2-dimethyl)-1,3-dioxolane acetamide (185996-33-2) → [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine (82954-65-2,96894-67-6)

Guidance literature:

With sodium hydroxide; sodium hypochlorite; In water; at 50 - 60 ℃; for 24h;

DOI:10.1021/jo9818226

upstream raw materials:

methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate

2,2-dimethoxy-propane

(S)-3,4-dihydroxybutyramide

Downstream raw materials:

[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine

4-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-thiazole

4-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4,5-dihydro-thiazol-4-ol

Refernces

• 1、 Wang, Guijun,Hollingsworth, Rawle I.. "Direct conversion of (S)-3-hydroxy-γ-butyrolactone to chiral three- carbon building blocks". . p. 1036 - 1038. Retrieved 2007/10/03.