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551-16-6

Basic Information
CAS No.: 551-16-6
Name: 6-Aminopenicillanic acid
Molecular Structure:
Molecular Structure of 551-16-6 (6-Aminopenicillanic acid)
Formula: C8H12N2O3S
Molecular Weight: 216.25
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;
EINECS: 208-993-4
Density: 1.52 g/cm3
Melting Point: 198-200 °C (dec.)(lit.)
Boiling Point: 460.2 °C at 760 mmHg
Flash Point: 232.1 °C
Solubility: Soluble in water and hydrochoric acid.
Appearance: White to cream fine powder
Hazard Symbols: HarmfulXn
Risk Codes: 42/43
Safety: 22-36/37-45-37-24-36
Transport Information:
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrazine In tetrahydrofuran
61-33-6

penicillin G

A

103-82-2

phenylacetic acid

B

551-16-6

6-Aminopenicillanic Acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
Hydrolysis;
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With penicillin G acylase; water at 20℃; Enzymatic reaction;
551-16-6

6-Aminopenicillanic Acid

C8H12N2O3S*C7H12N2

Conditions
ConditionsYield
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
ConditionsYield
In dichloromethane at 20℃; for 1.5h;99%
551-16-6

6-Aminopenicillanic Acid

24158-88-1

6,6-dibromopenicillanic acid

Conditions
ConditionsYield
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 dichloromethane85%
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
ConditionsYield
With triethylamine In dichloromethane for 0.5h;97%
551-16-6

6-Aminopenicillanic Acid

69-53-4

ampicillin

Conditions
ConditionsYield
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
ConditionsYield
In ethanol; acetic acid at 40℃; for 72h;96%
551-16-6

6-Aminopenicillanic Acid

13789-47-4

6-aminopenicillanic acid methyl ester

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
In methanol for 16h;94%
551-16-6

6-Aminopenicillanic Acid

1885-14-9

phenyl chloroformate

63019-62-5

phenoxycarbonylaminopenicillanic acid

Conditions
ConditionsYield
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
ConditionsYield
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%
551-16-6

6-Aminopenicillanic Acid

6674-22-2

1,8-diazabicyclo[5.4.0]undec-7-ene

C8H12N2O3S*C9H16N2

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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
ConditionsYield
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
ConditionsYield
In water at 20℃; for 24h;90%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With triethylamine In acetone at 30℃; for 24h;88%
551-16-6

6-Aminopenicillanic Acid

87-53-6

penicillanic acid

Conditions
ConditionsYield
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

Conditions
ConditionsYield
With chloro-trimethyl-silane; triethylamine In dichloromethane87.6%
551-16-6

6-Aminopenicillanic Acid

908093-98-1

diazodiphenylmethane

47547-28-4, 78184-79-9

6-aminopenicillanic acid diphenylmethyl ester

Conditions
ConditionsYield
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
ConditionsYield
In ethanol; acetic acid at 40℃; for 72h;86%
551-16-6

6-Aminopenicillanic Acid

A

875-74-1

(R)-phenylglycine

B

69-53-4

ampicillin

Conditions
ConditionsYield
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%
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
ConditionsYield
In water; acetone for 1h;85%
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Chemistry

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

Uses

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

Toxicity Data With Reference

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

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: HarmfulXn
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 NOx and SOx.

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