Name: sodium 6-(2,6-dimethoxybenzamido)penicillanate
SKU: 132-92-3

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Basic Information

CAS No.:

132-92-3

Name:

sodium 6-(2,6-dimethoxybenzamido)penicillanate

Molecular Structure:

Formula:

C17H20 N2 O6 S . Na

Molecular Weight:

402.403

Synonyms:

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-, monosodium salt (8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, monosodium salt,(2S,5R,6R)- (9CI); 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-, monosodium salt, [2S-(2a,5a,6b)]-; Azapen; BRL 1241; Belfacillin; Celbenin; Celpillina; Celpilline;Cinopenil; Dimethoxyphenecillin sodium; Dimocillin; Dimocillin sodium;Dimocillin-R-2; Estafcilina; Flabelline; Lucopenin; Methicillin sodium;Methicillin sodium salt; Meticillin sodium; Meticillin sodium salt; Penaureus;Penistaph; Penysol; SQ 16123; Sodium (2,6-dimethoxyphenyl)penicillin; Sodium6-(2,6-dimethoxybenzamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;Sodium 6-(2',6'-dimethoxybenzamido)penicillanate; Sodiumdimethoxyphenylpenicillin; Sodium methicillin; Staficyn; Staphcillin;Synticillin; X-1497

Density:

g/cm³

Melting Point:

196-197℃

Boiling Point:

640°Cat760mmHg

Flash Point:

340.9°C

Solubility:

Slightly soluble in acetone. Soluble in ethanol or water

Hazard Symbols:

Risk Codes:

36/37/38-42/43

Safety:

Hazard Codes	Xn
Risk Statements	36/37/38-42/43
Safety Statements	26-36
RTECS	XH8950000

PSA:

133.30000

LogP:

-0.05680

Synthetic route

: 18997-19-8
Chloromethyl pivalate

: 132-92-3
methicillin sodium

: 104430-18-4
methicillin t. butylcarbonyloxymethyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 6h; Ambient temperature;	56%

: 132-92-3
methicillin sodium

: 57414-10-5
(4S)-2t-[(2,6-dimethoxy-benzoylamino)-methyl]-5,5-dimethyl-thiazolidine-4r-carboxylic acid

Conditions

Conditions	Yield
(i) aq. NaOH, (ii) aq. EtOH; Multistep reaction;

: 132-92-3
methicillin sodium

: 106215-27-4
(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid

Conditions

Conditions	Yield
With hydrogen cation; 4-methyl-2-pentanone for 168h; Ambient temperature;

: 132-92-3
methicillin sodium

: 3568-15-8
N-[2-(2,6-dimethoxy-phenyl)-5-oxo-oxazol-4-ylidenemethyl]-D-penicillamine

Conditions

Conditions	Yield
(i) aq. HgCl2, (ii) aq. H2S; Multistep reaction;

: 49715-04-0
chlorosulfuric acid chloromethyl ester

: 132-92-3
methicillin sodium

: 34582-70-2
chloromethyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane; water for 0.5h; below 30 deg C;	4.24 g
With sodium hydrogencarbonate; tetra(n-butyl)ammonium hydrogen sulfate In dichloromethane; water

: 132-92-3
methicillin sodium

: 122648-61-7
<(3-pyridinylcarbonyl)oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C 2: 3 g / dimethylformamide / 144 h / Ambient temperature View Scheme

: 132-92-3
methicillin sodium

: 122648-68-4
<<(1,4-dihydro-1-methyl-3-pyridinyl)carbonyl>oxy>methyl <2S-(2α,5α,6β)>-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C 2: 3 g / dimethylformamide / 144 h / Ambient temperature 3: 1.6 g / nitromethane / 168 h / 20 - 25 °C 4: 0.25 g / Na2S2O4, NaHCO3 / ethyl acetate; H2O / 1.17 h / 0 - 5 °C View Scheme

: 132-92-3
methicillin sodium

: <2S-(2α,5α,6β)>-3-<<<<<3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)-4-thia-1-azabicyclo<3.2.0>hept-2-yl>carbonyl>oxy>methoxy>carbonyl>-1-methylpyridinium iodide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 4.24 g / NaHCO3, tetrabutylammonium hydrogen sulfate / H2O; CH2Cl2 / 0.5 h / below 30 deg C 2: 3 g / dimethylformamide / 144 h / Ambient temperature 3: 1.6 g / nitromethane / 168 h / 20 - 25 °C View Scheme

: 132-92-3
methicillin sodium

: 104430-22-0
(2R,4S)-2-[(R)-(2,6-Dimethoxy-benzoylamino)-hydroxycarbamoyl-methyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 56 percent / dimethylformamide / 6 h / Ambient temperature 2: 100 percent / hydroxylaminehydrochloride, NaOH / methanol / 1.) -30 deg C to 20 deg C for 1h, 2.) room temperature, 1h View Scheme

: 132-92-3
methicillin sodium

: 106095-84-5
(6aR)-6t,12t-bis-(2,6-dimethoxy-benzoylamino)-2,2,8,8-tetramethyl-5,11-dioxo-(6ar,12ac)-octahydro-bisthiazolo[3,2-a;3',2'-e][1,5]diazocine-3c,9c-dicarboxylic acid dimethyl ester