6-{[Amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Base Information

• Chemical Name: 6-{[Amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS No.: 26787-78-0
• Molecular Formula: C16H19N3O5S
• Molecular Weight: 365.41
• Hs Code.: H19N3O5S-3H2O MOL WT. 419.45
• NSC Number: 277174
• DSSTox Substance ID: DTXSID50860378
• Nikkaji Number: J25.703F
• Wikidata: Q105156722
• Mol file: 26787-78-0.mol

Synonyms:Amoxicillin-13C2,15N(MixtureofDiastereomers);Amoxicillin (trihydrate);Amoxycillin (trihydrate);6-{[amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;SCHEMBL226659;DTXSID50860378;HMS3372L05;(2S,5R,6R)-6-[[(2S)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-;STL140785;AKOS005715796;.alpha.-Amino-p-hydroxybenzylpenicillin;AC-15069;D-(.alpha.-Amino-p-hydroxybenzyl)penicillin;FT-0602856;D-(-)-.alpha.-Amino-p-hydroxybenzylpenicillin;EN300-296143;D-(-)-.alpha.-Amino-p-hydroxybenzyl penicillin;WLN: T45 ANV ESTJ CMVYZR DQ& F1 F1 GVQ;6-[D-(-)-p-Hydroxy-.alpha.-aminobenzyl]penicillin;6-(p-Hydroxy-.alpha.-aminophenylacetamido)penicillanic acid;6[D(-).alpha.-Amino-p-hydroxyphenylacetamido]penicillanic acid;3,3-Dimethyl-6-(alpha-oxo-beta-amino-4-hydroxyphenethylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,3-dimethyl-7-oxo- [2S[2.alpha.,5.alpha.,6.beta.(S*)]];6-(2-amino-2-(4-hydroxyphenyl)acetamido)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid;6-[2-Amino(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-[2-amino-2-(4-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;6-[D-(-)-2-Amino-2-(p-hydroxyphenyl)acetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Chemical Property of 6-{[Amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.39E-23mmHg at 25°C
• Melting Point: 140 °C
• Boiling Point: 743.2 °C at 760 mmHg
• PKA: pKa 2.4 (Uncertain)
• Flash Point: 403.3 °C
• PSA: 158.26000
• Density: 1.54 g/cm³
• LogP: 1.05280
• Storage Temp.: 2-8°C
• Solubility.: Do you have solubility information on this product that you woul
• Water Solubility.: 4g/L at 25℃
• XLogP3: -2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 365.10454189
• Heavy Atom Count: 25
• Complexity: 590

Purity/Quality:

≥99.0% ^*data from raw suppliers

Amoxicillin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 42/43
• Safety Statements: 22-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
• Uses: Antibacterial;Bacterial transpeptidase inhibitor Amoxicillin is an antibiotic used in the treatment of various bacterial infections.
• Indications: Amoxycillin, like ampicillin, has a broad spectrum of use. Indications for use are the same as with ampicillin. Synonyms of this drug are amoxican, amoxil, larotid, robamox, trimox, vimox, utimox, and others. Undoubtedly, analogs of ampicillin that are substituted at the amine fragment of phenylglycine (azolcillin, mezlocillin, piperacillin) should be included in this same group of compounds.
• Therapeutic Function: Antibacterial
• Clinical Use: Amoxicillin, 6-[D-(－)-α-amino-p- hydroxyphenylacetamido]penicillanic acid (Amoxil, Larotid, Polymox), a semisyntheticpenicillin introduced in 1974, is simply the p-hydroxyanalog of ampicillin, prepared by acylation of 6-APA with phydroxyphenylglycine.Its antibacterial spectrum is nearly identical with that ofampicillin, and like ampicillin, it is resistant to acid, susceptibleto alkaline and β-lactamase hydrolysis, andweakly protein bound. Early clinical reports indicated thatorally administered amoxicillin possesses significantadvantages over ampicillin, including more complete GIabsorption to give higher plasma and urine levels, lessdiarrhea, and little or no effect of food on absorption.50Thus, amoxicillin has largely replaced ampicillin for thetreatment of certain systemic and urinary tract infectionsfor which oral administration is desirable. Amoxicillin isreportedly less effective than ampicillin in the treatment ofbacillary dysentery, presumably because of its greater GIabsorption. Considerable evidence suggests that oral absorptionof α-aminobenzyl–substituted penicillins (e.g.,ampicillin and amoxicillin) and cephalosporins is, at leastin part, carrier mediated, thus explaining their generallysuperior oral activity.Amoxicillin is a fine, white to off-white, crystallinepowder that is sparingly soluble in water. It is available invarious oral dosage forms. Aqueous suspensions are stablefor 1 week at room temperature. Isolates should be tested for susceptibility before use, especially for serious infections.Ear, nose and throat infections other than pharyngitis, which may mask glandular fever Tracheobronchitis, bronchitis, pneumonia Genitourinary tract infections, including gonorrhea Infections of skin and soft tissues due to streptococci and susceptible staphylococci Helicobacter pylori infection (in combination with a proton pump inhibitor and at least one other antimicrobial agent such as clarithromycin) Prophylaxis of endocarditis in patients undergoing dental treatment and other procedures
• Drug interactions: Potentially hazardous interactions with other drugs Amoxicillin can reduce the excretion of methotrexate (increased risk of toxicity).

Technology Process of 6-{[Amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

There total 25 articles about 6-{[Amino(4-hydroxyphenyl)acetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 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: 62.0%

C31H29N3O7S → amoxicillin (26787-78-0,81030-75-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; for 3h;

Reference yield:

6-aminopenicillanic acid (551-16-6,1079-37-4,3115-55-7,21794-93-4,145920-51-0) → amoxicillin (26787-78-0,81030-75-3) + 2-ethylhexanoic acid chloride (760-67-8)

Guidance literature:

Reference yield:

C24H25N3O7S → amoxicillin (26787-78-0,81030-75-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; water; for 3h;

upstream raw materials:

6-Aminopenicillanic Acid

D-2-p-hydroxyphenylglycine methyl ester

methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride

oxirane

Downstream raw materials:

6β-[(R)-2-formylamino-2-(4-hydroxy-phenyl)-acetylamino]-penicillanic acid

Refernces

• 1、 Hsi, Kay Huai Ying,Concepcion, Anthony Joseph,Kenny, Meghan,Magzoub, Amna Ahmed,Myerson, Allan S.. "Purification of amoxicillin trihydrate by impurity-coformer complexation in solution". . p. 6776 - 6781. Retrieved 2013.
• 2、 -. "Preparation method of amoxicillin". Paragraph 0033-0035. . Retrieved 2019/12/25.