36923-17-8

Basic information

• Product Name: 7-Amino-3-cephem-4-carboxylic acid
• Synonyms: 7-amino-8-oxo,(6R,7R)-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid;7-AMINO-3-NOR CEPHALOSPORANIC ACID(7-ANCA);5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-amino-8-oxo,(6R,7R)-;7-AMOCA;7-ANCA 7-Amino-3-cephem-4-carboxylic acid;(6R,7R)-7-AMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;(6R-trans)-7-AMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;7-PACA [(6R,7R)-7-AMINO-3[(Z/E)]-1-PROPEN-1-YL)-3-CEPHEM-4-CARBOXYLIC-ACID)
• CAS NO: 36923-17-8
• Molecular Formula: C₇H₈N₂O₃S
• Molecular Weight: 200.22
• EINECS: 1308068-626-2
• Product Categories: Organic acids;Amines;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 36923-17-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 215-218°C
• Boiling Point: 536.9 °C at 760 mmHg
• Flash Point: 278.5 °C
• Appearance: /
• Density: 1.699g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.735
• Storage Temp.: -20?C Freezer
• Solubility: Aqueous Acid (Slightly, Heated), DMSO (Slightly)
• PKA: 2.92±0.50(Predicted)
• CAS DataBase Reference: 7-Amino-3-cephem-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Amino-3-cephem-4-carboxylic acid(36923-17-8)
• EPA Substance Registry System: 7-Amino-3-cephem-4-carboxylic acid(36923-17-8)

Safety Data

• Hazardous Substances Data: 36923-17-8(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

7-Amino-3-cephem-4-carboxylic acid is a reagent used in the preparation of Cephalosporin antibiotics.

InChI:InChI=1/C7H8N2O3S/c8-4-5(10)9-3(7(11)12)1-2-13-6(4)9/h1,4,6H,2,8H2,(H,11,12)/t4-,6-/m1/s1

Synthetic route

C7H9IN2O3S → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
With potassium hydroxide In methanol; water at 25 - 30℃; for 5h; pH=8 - 8.5;	90.85%

C14H13N3O5S*ClH → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
With trimethylsilyl bromide In dichloromethane at 20 - 25℃; for 5.5h;	89%

diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (36923-21-4) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
With methoxybenzene; trifluoroacetic acid

(6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (35246-64-1) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: (PhCO)2O / dimethylsulfoxide / Ambient temperature 2: <(Ph3P)3Rh>Cl / benzene 3: (i) PCl5, Py, (ii) MeOH 4: PhOMe, CF3CO2H View Scheme

diphenylmethyl (6R,7R)-7-(phenylacetamido)ceph-3-em-4-carboxylate (36923-19-0) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) PCl5, Py, (ii) MeOH 2: PhOMe, CF3CO2H View Scheme

(6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (35246-65-2) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: <(Ph3P)3Rh>Cl / benzene 2: (i) PCl5, Py, (ii) MeOH 3: PhOMe, CF3CO2H View Scheme

p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate (53116-50-0) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: diphenylsilyl chloride; aluminum (III) chloride / dichloromethane / 4 h / 15 - 25 °C 2.1: diisooctyl phenyl phosphite; bromine; 1H-imidazole / dichloromethane / 5 h / -45 - -40 °C 2.2: 0.5 h 3.1: trimethylsilyl bromide / dichloromethane / 5.5 h / 20 - 25 °C View Scheme

(6R,7R)-1-aza-3-chloro-7-amino-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (53994-69-7) → (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; ammonium hydroxide / water; methanol / 0.5 h / 15 - 25 °C / pH 7 - 7.5 2: sodium iodide; glycine; sodium hydrogencarbonate / acetone / 4 h / 25 - 30 °C / Sonication 3: potassium hydroxide / water; methanol / 5 h / 25 - 30 °C / pH 8 - 8.5 View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + C13H10N4O2S3 → ceftizoxime (68401-81-0)

Conditions	Yield
Stage #1: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With dmap In dichloromethane at -8 - 0℃; Stage #2: C13H10N4O2S3 With dmap In dichloromethane at -5 - 0℃; for 0.25h; Reagent/catalyst; Temperature;	97%

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + {(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-[2-(trityl-amino)-thiazol-4-yl]-acetic acid (159048-31-4) → (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1026067-63-9)

Conditions	Yield
With pyridine; trichlorophosphate Substitution;	96%

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + 1-benzyl-4-fluoropyridinium bromide (77527-66-3) → C19H17N3O3S (79601-77-7)

Conditions	Yield
With sodium hydroxide In water at 22℃; pH 7;	54%

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + 2-<(2-14C)-2-formylamino-4-thiazolyl>-(Z)-2-methoxyimino acetic acid → C13(14)CH13N5O6S2

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + diazodiphenylmethane (908093-98-1) → diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (36923-21-4)

Conditions	Yield
In acetonitrile

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → C21H15N7O9S2(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 96 percent / POCl3; pyridine 2.1: trifluoracetic acid / methoxybenzene / purified by chromatography and lyophilization 2.2: 81 percent / NaHCO3 View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(2-methoxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: acetonitrile 2: 63 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 99 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(2-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: acetonitrile 2: 69 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 100 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(3-hydroxy-pyridyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: acetonitrile 2: 62 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 86 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(2,6-dihydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: acetonitrile 2: 55 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h 3: 86 percent / Et3SiH, trifluoroacetic acid / 1,2-dichloro-ethane / 0 °C View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(3-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester (171017-68-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile 2: 63 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(2-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester (171017-57-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile 2: 69 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(3-hydroxy-2-pyridyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester (171017-65-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile 2: 62 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → (6R,7R)-7-<2-(2,6-dihydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester (171017-61-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetonitrile 2: 55 percent / morpho CDI / tetrahydrofuran; CH2Cl2 / 1.) 0 deg C, 24 h, 2.) 25 deg C, 5 h View Scheme

2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid (91868-79-0) + (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → cefotaxime sodium salt (64485-93-4)

Conditions	Yield
Stage #1: 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid With dmap; dicyclohexyl-carbodiimide In ethanol at 20℃; for 0.5h; Stage #2: With 1-hydroxy-pyrrolidine-2,5-dione In ethanol at 20℃; for 0.5h; Stage #3: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Further stages;	2.59 g

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) + (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) → ceftizoxime (68401-81-0)

Conditions	Yield
Stage #1: (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In chloroform for 0.333333h; Stage #2: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate In chloroform at 35℃; for 4.5h; Temperature;	87 g

Upstream product

• 53994-69-7 (6R,7R)-1-aza-3-chloro-7-amino-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene-2-carboxylic acid 
• 53116-50-0 p-nitrobenzyl 7-phenylacetamido-3-hydroxy-3-cephalosporin-4-carboxylate 
• 35246-65-2 (6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 36923-19-0 diphenylmethyl (6R,7R)-7-(phenylacetamido)ceph-3-em-4-carboxylate 
• 35246-64-1 (6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 36923-21-4 diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 108260-00-0 7-aminocephalosporanic acid 

Downstream Products

• 79601-77-7 C₁₉H₁₇N₃O₃S 
• 1026067-63-9 (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 68401-81-0 ceftizoxime 
• 64485-93-4 cefotaxime sodium salt 
• 171017-61-1 (6R,7R)-7-<2-(2,6-dihydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 171017-65-5 (6R,7R)-7-<2-(3-hydroxy-2-pyridyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 171017-57-5 (6R,7R)-7-<2-(2-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 171017-68-8 (6R,7R)-7-<2-(3-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 
• 36923-21-4 diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 

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