6-Aminopenicillanic acid supplier

Name
6-Aminopenicillanic acid
EINECS 208-993-4
CAS No. 551-16-6
Article Data58
CAS DataBase
Density 1.52 g/cm³
Solubility Soluble in water and hydrochoric acid.
Melting Point 198-200 °C (dec.)(lit.)
Formula C₈H₁₂N₂O₃S
Boiling Point 460.2 °C at 760 mmHg
Molecular Weight 216.261
Flash Point 232.1 °C
Transport Information
Appearance White to cream fine powder
Safety 22-36/37-45-37-24-36
Risk Codes 42/43
Molecular Structure
Hazard Symbols Xn
Synonyms 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-amino-3,3-dimethyl-7-oxo- (6CI,8CI);4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-amino-3,3-dimethyl-7-oxo-, [2S-(2a,5a,6b)]-;(+)-6-Aminopenicillanic acid;6-APA;6-APS;6b-Aminopenicillanic acid;NSC 50071;Phenacyl 6-aminopenicillinate;
PSA 108.93000
LogP 0.09880

Synthetic route

: 129096-81-7
(2S,5R,6R)-Benzyl 6-Azido-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate for 3h; Ambient temperature;	59%

: 61-33-6
penicillin G

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With penicillin-amidase from penicillium chrysogenum-stems
With penicillin G acylase; water at 28 - 29℃; pH=Ca. 8; Enzymatic reaction;

: 40124-92-3
6R(β)-tritylaminopenicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With hydrogenchloride; isopropyl alcohol
(i) aq. H3PO4, benzene, (ii) aq. HCl, iPrOH; Multistep reaction;

: 113-98-4
Penicillin G potassium

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multistep reaction;
With sodium hydroxide In aq. phosphate buffer at 55℃; pH=7.8; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; pH-value; Enzymatic reaction;

: 55151-71-8
6β-(3-oxo-3H-isobenzofuran-1-ylideneamino)-penicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With hydrazine In tetrahydrofuran

: 61-33-6
penicillin G

A: 103-82-2
phenylacetic acid

B: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With sodium hydroxide at 28℃; Equilibrium constant; penicillin G amidase (E.C. 3.5.1.11) immobilized on polyacrylamide, pH 8; var. substrate concentrations;
With penicillin G acylase immobilized on aminopropyl functionalized mesocellular foam silica crooslinked using glutaraldehyde In aq. phosphate buffer at 50℃; pH=7; Kinetics; pH-value; Temperature; Concentration; Reagent/catalyst; Enzymatic reaction;

penicillins to 6β-amino-penicillanic acid: penicillins to 6β-amino-penicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
fermentative und enzymatische Spaltung;
chemische Spaltung;
fermentative und enzymatische Spaltung;
chemische Spaltung;

: 61-33-6
penicillin G

penicillin-amidase: penicillin-amidase

penicillium chrysogenum-stems: penicillium chrysogenum-stems

A: 103-82-2
phenylacetic acid

B: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Hydrolysis;

...Expand

: 26939-76-4
(2S,5R,6R)-1-aza-3,3'-dimethyl-6-(4-carboxybutanamido)-7-oxo-4-thiabicyclo<3.2.0>heptane-2-carboxylic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
With sodium hydroxide; glutaryl-7-aminocephalosporanic acid acylase In water at 25℃; pH=8.0; Enzyme kinetics; Enzymatic reaction;

: 6-N-[3-(2,2,5,5-tetramethyl-1-oxypyrrolin-3-yl)-propen-2-oyl]penicillanic acid

A: 551-16-6
6-Aminopenicillanic Acid

B: 86073-81-6
(E)-3-(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)acrylic acid

Conditions

Conditions	Yield
With class A TEM-1 β-lactamase; HEPES buffer In water; dimethyl sulfoxide at 24℃; pH=7; Kinetics; Further Variations:; Reagents; Enzymatic reaction;

: 128971-90-4
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 90 percent / 2,6-lutidine / tetrahydrofuran / 2 h / -78 °C 2: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 4: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 6: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 7: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 8: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 9: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 9 steps
1: 90 percent / 2,6-lutidine / tetrahydrofuran / 2 h / -78 °C
2: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min
3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
4: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C
5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C
6: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature
7: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C
8: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature
9: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature
View Scheme

: 128971-96-0
(2S,5R,6S)-Benzyl 3,3-Dimethyl-7-oxo-6-<<(trifluoromethyl)sulfonyl>oxy>-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 2: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

: 128971-91-5
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min 2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 3: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 5: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 6: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 7: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 8: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 8 steps
1: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min
2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
3: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C
4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C
5: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature
6: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C
7: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature
8: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature
View Scheme

: 128971-92-6
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<(2-methyl-3-oxo-2-propyl)thio>-2-azetidinone

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h 2: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 3: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 4: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 5: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 6: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 7: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h
2: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C
3: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C
4: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature
5: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C
6: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature
7: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature
View Scheme

: 128971-93-7
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<<4-(benzyloxy)-3-hydroxy-2-methyl-4-nitro-2-butyl>thio>-2-azetidinone

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C 2: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 3: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 4: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 5: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 6: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 6 steps
1: 62 percent / Et3N, AcCl / CH2Cl2 / 20 h / 0 °C
2: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C
3: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature
4: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C
5: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature
6: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature
View Scheme

: 128971-94-8
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<<4-(benzyloxy)-2-methyl-4-nitro-3(Z)-buten-2-yl>thio>-2-azetidinone

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH2Cl2, -78 deg C 2: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 3: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 4: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 5: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

: 15139-36-3, 51056-25-8, 128971-95-9
(2R,S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / DBU / CH2Cl2 / 8 h / Ambient temperature 2: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 3: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 4: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

: 51056-25-8
(2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 40 mg / Et3N / CH2Cl2 / 0.25 h / 0 °C 2: 90 percent / LiN3 / dimethylformamide / 18 h / Ambient temperature 3: 59 percent / H2 / 10 percent Pd/C / ethyl acetate / 3 h / Ambient temperature View Scheme

: 21027-18-9
methyl 6β-(triphenylmethylamino)penicillinate

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous NaOH; pyridine 2: aqueous HCl; isopropyl alcohol View Scheme

: 20425-27-8
(2S,5R,6R)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Na2S*9H2O / acetone; H2O 2: DCC 3: N2H4 / tetrahydrofuran View Scheme

: 47449-42-3
6β-(2-carboxy-benzoylamino)-penicillanic acid

: 551-16-6
6-Aminopenicillanic Acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: DCC 2: N2H4 / tetrahydrofuran View Scheme

: 87-08-1
penicilin V

A: 551-16-6
6-Aminopenicillanic Acid

B: 122-59-8
2-phenoxyacetic acid

Conditions

Conditions	Yield
With ammonia; pen V amidase In water pH=8.2; Enzymatic reaction;

: 69-53-4
ampicillin

A: 551-16-6
6-Aminopenicillanic Acid

B: 875-74-1
(R)-phenylglycine

Conditions

Conditions	Yield
With α-amino ester hydrolase from Xanthomonas campestris pv. campestris (ATCC 33913) at 25℃; pH=7; Kinetics; Reagent/catalyst; pH-value; Temperature; aq. phosphate buffer; Enzymatic reaction; chemospecific reaction;

: 26787-78-0
amoxicillin

A: 551-16-6
6-Aminopenicillanic Acid

B: 6324-01-2
p-hydroxyphenylglycine

Conditions

Conditions	Yield
With penicillin G acylase; water at 20℃; Enzymatic reaction;

: 551-16-6
6-Aminopenicillanic Acid

: 3001-72-7
DBN

: C8H12N2O3S*C7H12N2

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	100%

: 551-16-6
6-Aminopenicillanic Acid

: 80-70-6
N,N,N',N'-tetramethylguanidine

: C8H12N2O3S*C5H13N3

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	99%

: 551-16-6
6-Aminopenicillanic Acid

: 24158-88-1
6,6-dibromopenicillanic acid

Conditions

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite In water at -15 - -5℃; for 0.366667h; Time;	97.4%
Stage #1: 6-Aminopenicillanic Acid With sulfuric acid; hydrogen bromide; sodium nitrite In water at 0 - 5℃; for 1.5h; pH=Ca. 2.5; Stage #2: With dihydrogen peroxide In water at 0 - 5℃; for 1h;	93%
With sulfuric acid; bromine; sodium nitrite In dichloromethane	85%

: 551-16-6
6-Aminopenicillanic Acid

: 80543-51-7
(S)-formyloxy(phenyl)acetyl chloride

: 95107-10-1
(2'S,3S,5R,6R)-6-formyloxy(phenyl)acetylaminopenicillanic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 0.5h;	97%

: 551-16-6
6-Aminopenicillanic Acid

: 69-53-4
ampicillin

Conditions

Conditions	Yield
With (S)-Phenylglycine methyl ester In ethylene glycol at 20℃; for 48h; Enzymatic reaction;	96.7%

: 90-59-5
3,5-Dibromosalicylaldehyde

: 551-16-6
6-Aminopenicillanic Acid

: (2S,5R,6R)-6-{[1-(3,5-Dibromo-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Conditions

Conditions	Yield
In ethanol; acetic acid at 40℃; for 72h;	96%

: 186581-53-3, 908094-01-9
diazomethane

: 551-16-6
6-Aminopenicillanic Acid

: 13789-47-4
6-aminopenicillanic acid methyl ester

Conditions

Conditions	Yield
In dichloromethane at 20℃;	95%
In dichloromethane at 20℃; for 1h;	95%
In diethyl ether; water

: 551-16-6
6-Aminopenicillanic Acid

: 18997-19-8
Chloromethyl pivalate

: 25031-08-7
(pivaloyloxy)methyl 6β-aminopenicillinate

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; acetonitrile at 20℃; for 1h;	95%
With triethylamine In N,N-dimethyl-formamide Ambient temperature;
With triethylamine In N,N-dimethyl-formamide

: 551-16-6
6-Aminopenicillanic Acid

: 2065-23-8
methyl 2-phenoxyacetate

: 87-08-1
penicilin V

Conditions

Conditions	Yield
With recombinant Streptomyces lavendulae penicillinacylase In dimethyl sulfoxide at 30℃; for 10.8h; pH=7; Catalytic behavior; Kinetics; Concentration; pH-value; Solvent; Time; Enzymatic reaction;	94.5%

: 551-16-6
6-Aminopenicillanic Acid

: 29169-64-0
D-2-phenyl-2-formyloxyacetyl chloride

: 95107-09-8
(2'R,3S,5R,6R)-6-formyloxy(phenyl)acetylaminopenicillanic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane for 0.5h;	94%

: 551-16-6
6-Aminopenicillanic Acid

: 123-54-6
acetylacetone

: 81651-32-3
6β-(1-methyl-3-oxobut-1-enylamino)penicillanic acid

Conditions

Conditions	Yield
In methanol for 16h;	94%

: 551-16-6
6-Aminopenicillanic Acid

: 1885-14-9
phenyl chloroformate

: 63019-62-5
phenoxycarbonylaminopenicillanic acid

Conditions

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; water at 5 - 10℃; pH 7-8;	92%

: 551-16-6
6-Aminopenicillanic Acid

: 103-71-9
phenyl isocyanate

: 121-44-8
triethylamine

: 53093-29-1
triethylammonium (2S,5R,6R)-6-[(anilinocarbonyl)amino]-penicillanate

Conditions

Conditions	Yield
Stage #1: 6-Aminopenicillanic Acid; triethylamine In N,N-dimethyl-formamide at -5℃; for 0.5h; Stage #2: phenyl isocyanate In N,N-dimethyl-formamide at 20℃; for 3.25h;	92%

...Expand

: 551-16-6
6-Aminopenicillanic Acid

: 6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

: C8H12N2O3S*C9H16N2

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	92%

: 551-16-6
6-Aminopenicillanic Acid

: 6,6-dimethyl-3-phenyl-1,5,2-dioxathiane-4-one-2,2-dioxide

: 28002-18-8, 36417-90-0, 36417-91-1, 37544-62-0, 76194-04-2
(2S,5R,6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt

Conditions

Conditions	Yield
Stage #1: 6-Aminopenicillanic Acid With N,O-bis-(trimethylsilyl)-acetamide In acetone at 30 - 35℃; for 3h; Stage #2: 6,6-dimethyl-3-phenyl-1,5,2-dioxathiane-4-one-2,2-dioxide In acetone at 40 - 45℃; for 5h; Stage #3: With sodium 2-ethylhexanoic acid In water; acetone at 5 - 20℃; for 2h; Temperature;	91.5%

6-Aminopenicillanic Acid: 6-Aminopenicillanic Acid

: 24138-28-1
6-bromopenicillanic acid

: 590-42-1
tert-butyl isothiocyanate

: 551-16-6
6-Aminopenicillanic Acid

: 121-44-8
triethylamine

: 1584804-32-9
triethylammonium (2S,5R,6R)-6-{[(tert-butylamino)-carbonothioyl]amino}penicillanate

Conditions

Conditions	Yield
Stage #1: 6-Aminopenicillanic Acid; triethylamine In N,N-dimethyl-formamide at -5℃; for 0.5h; Stage #2: tert-butyl isothiocyanate In N,N-dimethyl-formamide at 20℃; for 3.25h;	91%

...Expand

: 551-16-6
6-Aminopenicillanic Acid

: 5350-57-2
benzophenone hydrazone

: diphenylmethyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

Conditions

Conditions	Yield
With peracetic acid In dichloromethane; water; acetone at -5 - 5℃; for 1h;	91%

: 551-16-6
6-Aminopenicillanic Acid

: 124-38-9
carbon dioxide

: 144-55-8
sodium hydrogencarbonate

: 8-hydroxypenillic acid (3,3-dimethyl-8-oxo-4-thia-1,7-diazabicyclo[3.3.0]octane-2,6-dicarboxylic acid) disodium

Conditions

Conditions	Yield
In water at 20℃; for 24h;	90%

...Expand

: 551-16-6
6-Aminopenicillanic Acid

: 124-38-9
carbon dioxide

: 8-hydroxypenillic acid (3,3-dimethyl-8-oxo-4-thia-1,7-diazabicyclo[3.3.0]octane-2,6-dicarboxylic acid) disodium

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water at 20℃; for 24h;	90%

: 551-16-6
6-Aminopenicillanic Acid

: 24424-99-5
di-tert-butyl dicarbonate

: 26531-14-6
(2S,5R,6R)-6-(tert-butoxycarbonylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃; for 24h;	90%
With triethylamine In 1,4-dioxane; water at 20℃; for 24h;
With triethylamine In dichloromethane at 20℃; for 5h;

: 551-16-6
6-Aminopenicillanic Acid

: 41360-32-1
racemic α-sulfophenylacetic acid

: 28002-18-8, 36417-90-0, 36417-91-1, 37544-62-0, 76194-04-2
(2S,5R,6R)-3,3-dimethyl-6-(2-phenyl-2-sulfoacetylamino)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid disodium salt

Conditions

Conditions	Yield
Stage #1: racemic α-sulfophenylacetic acid With triethanolamine; 1,1'-carbonyldiimidazole In dichloromethane; toluene at -10℃; for 1.5h; Stage #2: 6-Aminopenicillanic Acid In dichloromethane; water; isopropyl alcohol; acetone; toluene at -5 - 10℃; for 0.75h; Stage #3: With sodium hydroxide In water pH=6 - 7; Concentration; Solvent;	88.1%
Stage #1: racemic α-sulfophenylacetic acid With propionyl chloride; triethylamine In dichloromethane at 0 - 25℃; for 3h; Stage #2: 6-Aminopenicillanic Acid With 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide In ethyl acetate at 50℃; for 2h; Inert atmosphere; Stage #3: With hydrogenchloride; sodium isooctanoate In ethanol; water at 0 - 25℃; for 0.75h; Reflux;	84%

: 551-16-6
6-Aminopenicillanic Acid

: 501-53-1
benzyl chloroformate

: 23536-59-6
<2S-<2α,5α,6β>>-3,3-dimethyl-7-oxo-6-<<(phenylmethoxy)carbonyl>amino>-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; water for 2h;	88%

: 551-16-6
6-Aminopenicillanic Acid

: 3757-06-0
coumarin 3-carboxylic acid chloride

: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(2-oxo-2H-chromene-3-carbonyl)-amino]-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In acetone at 30℃; for 24h;	88%

: 551-16-6
6-Aminopenicillanic Acid

: 87-53-6
penicillanic acid

Conditions

Conditions	Yield
Stage #1: 6-Aminopenicillanic Acid With sulfuric acid; sodium nitrite In water at -10 - 5℃; for 1h; Stage #2: With sodium hypophosphite In water at -5 - 30℃; for 2h;	88%
Multi-step reaction with 2 steps 1: NaBr, NaNO2 / H2SO4; H2O / 1 h / 0 °C 2: hydrogen / 5 percent palladium-on-CaCO3 / various solvent(s) / 24 h / 20 °C / 2068.6 Torr View Scheme
Stage #1: 6-Aminopenicillanic Acid With hydrogenchloride; sodium nitrite In water at -5℃; for 5h; Stage #2: With hypophosphorous acid; copper In ethanol; dichloromethane; water at 5℃; for 3h; Solvent; Reagent/catalyst; Heating;

: 57397-48-5
N,N-Bis(trimethylsilyl)urea

: 551-16-6
6-Aminopenicillanic Acid

: 5187-94-0, 7177-48-2, 32388-53-7, 57095-77-9, 145454-26-8
ampicillin trihydrate

Conditions

Conditions	Yield
With chloro-trimethyl-silane; triethylamine In dichloromethane	87.6%

: 551-16-6
6-Aminopenicillanic Acid

: 908093-98-1
diazodiphenylmethane

: 47547-28-4, 78184-79-9
6-aminopenicillanic acid diphenylmethyl ester

Conditions

Conditions	Yield
In methanol; dichloromethane at 20℃;	87%
In methanol; dichloromethane at 20℃; for 15h;	40%
With methanol In dichloromethane

: 551-16-6
6-Aminopenicillanic Acid

: 90-60-8
3,5-dichlorosalicyclaldehyde

: (2S,5R,6R)-6-{[1-(3,5-Dichloro-2-hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid

Conditions

Conditions	Yield
In ethanol; acetic acid at 40℃; for 72h;	86%

: 551-16-6
6-Aminopenicillanic Acid

: 700-63-0, 6485-52-5, 6485-67-2, 58429-87-1
(R)-phenylglycine amide

A: 875-74-1
(R)-phenylglycine

B: 69-53-4
ampicillin

Conditions

Conditions	Yield
With A. faecalis; immobilised penicillin acylase (EC 3.5.1.11) In water; acetonitrile at 0℃; Product distribution; Kinetics; Further Variations:; Solvents; reusing run; Enzymatic reaction;	A n/a B 86%

...Expand

: 551-16-6
6-Aminopenicillanic Acid

: 104-15-4
toluene-4-sulfonic acid

: 908093-98-1
diazodiphenylmethane

: 34642-75-6
Diphenylmethyl 6-aminopenicillanate p-toluenesulphonic acid salt

Conditions

Conditions	Yield
In water; acetone for 1h;	85%

...Expand

6-Aminopenicillanic acid Chemical Properties

Chemical Name: 6-Aminopenicillanic acid
IUPAC NAME: (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS No.: 551-16-6
EINECS: 208-993-4
Molecular Formula of Phenacyl 6-aminopenicillinate (CAS No.551-16-6): C₈H₁₂N₂O₃S
Molecular Weight: 216.26 g/mol
Structure:

Synonyms of Phenacyl 6-aminopenicillinate (CAS No.551-16-6): (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure ; 6-Aminopenicillanic acid ; 6-Apa ; 6-Aps ; AI3-52557 ; EINECS 208-993-4 ; NSC 50071 ; Penicin ; Penin ; Phenacyl 6-aminopenicillinate ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)- ; 6-Aminopenicillamine acid
Polar Surface Area: 75.15 Å²
Index of Refraction: 1.656
Molar Refractivity: 52.22 cm³
Molar Volume: 142 cm³
Surface Tension: 74.4 dyne/cm
Density of Phenacyl 6-aminopenicillinate (CAS No.551-16-6): 1.52 g/cm³
Flash Point: 232.1 °C
Enthalpy of Vaporization: 78.99 kJ/mol
Boiling Point: 460.2 °C at 760 mmHg
Vapour Pressure: 9.54E-10 mmHg at 25°C

6-Aminopenicillanic acid Uses

Phenacyl 6-aminopenicillinate (CAS No.551-16-6) is used as a pharmaceutical intermediate and antibiotics for research and experimental

6-Aminopenicillanic acid Toxicity Data With Reference

mouse LD50 intraperitoneal > 1gm/kg (1000mg/kg) National Technical Information Service. Vol. AD691-490,

6-Aminopenicillanic acid Consensus Reports

Reported in EPA TSCA Inventory.

6-Aminopenicillanic acid Safety Profile

Hazard Codes: Harmful Xn
Risk Statements: 42/43
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 22-36/37-45-24
S22: Do not breathe dust.
S36/37: Wear suitable protective clothing and gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24: Avoid contact with skin.
WGK Germany: 2
RTECS: XH8225000
F: 10
HS Code: 29349990
Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.

Product Name

6-Aminopenicillanic acid

Synthetic route

6-Aminopenicillanic acid Chemical Properties

6-Aminopenicillanic acid Uses

6-Aminopenicillanic acid Toxicity Data With Reference

6-Aminopenicillanic acid Consensus Reports

6-Aminopenicillanic acid Safety Profile

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