Tigecycline supplier | CasNO.220620-09-7

Name
Tigecycline
EINECS 685-736-6
CAS No. 220620-09-7
Article Data16
CAS DataBase
Density 1.455 g/cm³
Solubility
Melting Point 164-166°C
Formula C₂₉H₃₉N₅O₈
Boiling Point 890.922 °C at 760 mmHg
Molecular Weight 585.657
Flash Point 492.612 °C
Transport Information
Appearance Powder
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-;N-[(5aR,6aS,7S,9Z,10aS)-9-(amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-1,10a,12-trihydroxy-8,10,11-trioxo-5a,6,6a,7-tetrahydro-5H-tetracen-2-yl]-2-(tert-butylamino)acetamide;Tygacil (TN);Tygacil;(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
PSA 205.76000
LogP 1.67740

Synthetic route

: 156263-28-4
9-chloroacetamidominocycline

: 75-64-9
tert-butylamine

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl acetamide at 50℃; for 2h;	92%
Stage #1: 9-chloroacetamidominocycline; tert-butylamine With sodium iodide at 20℃; Stage #2: In water pH=5 - ~ 7.2; Product distribution / selectivity;	50%
With sodium iodide at 25 - 40℃; for 6h; Product distribution / selectivity;

: 2-(t-butylamino)acetyl chloride hydrochloride

: 9-amino-7-(dimethylamino)doxycycline hydrochloride

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
In water at 0 - 5℃; for 2h;	90%

: 2-(t-butylamino)acetyl chloride hydrochloride

: <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1h; Industry scale; Stage #2: With hydrogenchloride; ammonia In methanol; dichloromethane; water at 0 - 25℃; pH=0.42 - 7.4; Product distribution / selectivity;	77%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1h; Industry scale; Stage #2: With hydrogenchloride; ammonia In methanol; dichloromethane; water at 0 - 25℃; pH=0.42 - 7.4; Product distribution / selectivity;	77%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1h; Industry scale; Stage #2: With hydrogenchloride; ammonia In methanol; dichloromethane; water at 0 - 25℃; pH=0.42 - 7.4; Product distribution / selectivity;	77%

: 2-(t-butylamino)acetyl chloride hydrochloride

: 149934-19-0
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h; Stage #2: With ammonia In water at 0 - 5℃; pH=7.2; Product distribution / selectivity;	76.8%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h; Stage #2: With ammonia In methanol; dichloromethane; water at 0 - 5℃; for 0.25h; pH=7.2; Product distribution / selectivity;	76.8%
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h; Stage #2: With ammonia In methanol; dichloromethane; water at 0 - 5℃; for 0.25h; pH=7.2; Product distribution / selectivity;	76.8%

: 9-chloroacetamidominocycline hydrochloride

: 75-64-9
tert-butylamine

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: 9-chloroacetamidominocycline hydrochloride; tert-butylamine With sodium iodide at 20℃; Stage #2: In water pH=5 - ~ 7.2; Product distribution / selectivity;	35%

: 7065-46-5
3,3-dimethylbutanoic acid chloride

: 149934-19-0
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

: 220620-09-7
tigecycline

: 156263-28-4
9-chloroacetamidominocycline

: 75-64-9
tert-butylamine

A: Epitigecycline

B: 220620-09-7
tigecycline

Conditions

Conditions	Yield
With sodium iodide at 33 - 38℃; for 4h; Product distribution / selectivity;

...Expand

: 2-(t-butylamino)acetyl chloride hydrochloride

: 149934-19-0
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

A: Epitigecycline

B: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In water at 0 - 5℃; for 0.666667 - 1h; Stage #2: With ammonia In water at 0 - 5℃; pH=7.2; Product distribution / selectivity;
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In dichloromethane at 10 - 15℃; for 2h; Stage #2: With ammonia In methanol; dichloromethane; water at 5 - 8℃; pH=7.2; Product distribution / selectivity;
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide In N,N-dimethyl-formamide at 10 - 15℃; for 2h; Stage #2: With ammonia In methanol; water; N,N-dimethyl-formamide at 5 - 8℃; pH=7.2; Product distribution / selectivity;

...Expand

: 2-(t-butylamino)acetyl chloride hydrochloride

: <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride

A: Epitigecycline

B: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: 2-tert-butylaminoacetylchloride hydrochloride; <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide monohydrochloride In water at 0 - 6℃; for 1 - 3h; Stage #2: With ammonia In water at 0 - 10℃; pH=7.2; Product distribution / selectivity;

...Expand

: 2-(t-butylamino)acetyl chloride hydrochloride

: <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide disulfate

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: <4S-(4α,12aα)>-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide disulfate With sodium carbonate In water at 0℃; pH=2 - 3; Inert atmosphere; Stage #2: 2-tert-butylaminoacetylchloride hydrochloride With sodium carbonate In water at 0 - 30℃; pH=6.7; Inert atmosphere;

: N-t-butylglycine anhydride

: 149934-19-0
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: N-t-butylglycine anhydride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide With triethylamine; N-ethyl-N,N-diisopropylamine at 20℃; Stage #2: With sulfuric acid; potassium nitrate for 1h; Cooling with ice; Stage #3: With formaldehyd; palladium 10% on activated carbon; hydrogen In 2-methoxy-ethanol; water at 20℃; under 1520.1 Torr;

Yield

Stage #1: N-t-butylglycine anhydride; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide With triethylamine; N-ethyl-N,N-diisopropylamine at 20℃;
Stage #2: With sulfuric acid; potassium nitrate for 1h; Cooling with ice;
Stage #3: With formaldehyd; palladium 10% on activated carbon; hydrogen In 2-methoxy-ethanol; water at 20℃; under 1520.1 Torr;

: 58482-93-2
tert-butylaminoacetic acid

: 149934-19-0
[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: tert-butylaminoacetic acid; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide With triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; diisopropyl-carbodiimide at 20℃; for 3.333h; Stage #2: With sulfuric acid; potassium nitrate for 1h; Cooling with ice; Stage #3: With formaldehyd; palladium 10% on activated carbon; hydrogen In 2-methoxy-ethanol; water at 20℃; under 1520.1 Torr; for 10h; Reagent/catalyst;	4.139 g

Yield

Stage #1: tert-butylaminoacetic acid; [4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide With triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; diisopropyl-carbodiimide at 20℃; for 3.333h;
Stage #2: With sulfuric acid; potassium nitrate for 1h; Cooling with ice;
Stage #3: With formaldehyd; palladium 10% on activated carbon; hydrogen In 2-methoxy-ethanol; water at 20℃; under 1520.1 Torr; for 10h; Reagent/catalyst;

4.139 g

: Amicycline

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: water / 0 - 15 °C 2: sulfuric acid; potassium nitrate; nitric acid / -5 - 5 °C 3: rhodium contaminated with carbon; hydrogen / methanol / 12 h / 20 °C / 3000.3 Torr 4: palladium on activated charcoal; hydrogen / 2-methoxy-ethanol / 20 °C / 3000.3 Torr View Scheme

: C27H34N4O8

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid; potassium nitrate; nitric acid / -5 - 5 °C 2: rhodium contaminated with carbon; hydrogen / methanol / 12 h / 20 °C / 3000.3 Torr 3: palladium on activated charcoal; hydrogen / 2-methoxy-ethanol / 20 °C / 3000.3 Torr View Scheme

: 50-00-0
formaldehyd

: C27H35N5O8

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Stage #1: C27H35N5O8 With palladium on activated charcoal; hydrogen In 2-methoxy-ethanol at 20℃; under 3000.3 Torr; Stage #2: formaldehyd With hydrogen In methanol

: 127-33-3
Demeclocycline

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: sulfuric acid; potassium nitrate; nitric acid / 3 h / -5 - 5 °C 2: palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C / 30003 Torr 3: water / 0 - 15 °C 4: sulfuric acid; potassium nitrate; nitric acid / -5 - 5 °C 5: rhodium contaminated with carbon; hydrogen / methanol / 12 h / 20 °C / 3000.3 Torr 6: palladium on activated charcoal; hydrogen / 2-methoxy-ethanol / 20 °C / 3000.3 Torr View Scheme

Yield

Multi-step reaction with 6 steps
1: sulfuric acid; potassium nitrate; nitric acid / 3 h / -5 - 5 °C
2: palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C / 30003 Torr
3: water / 0 - 15 °C
4: sulfuric acid; potassium nitrate; nitric acid / -5 - 5 °C
5: rhodium contaminated with carbon; hydrogen / methanol / 12 h / 20 °C / 3000.3 Torr
6: palladium on activated charcoal; hydrogen / 2-methoxy-ethanol / 20 °C / 3000.3 Torr
View Scheme

: C21H22ClN3O8

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C / 30003 Torr 2: water / 0 - 15 °C 3: sulfuric acid; potassium nitrate; nitric acid / -5 - 5 °C 4: rhodium contaminated with carbon; hydrogen / methanol / 12 h / 20 °C / 3000.3 Torr 5: palladium on activated charcoal; hydrogen / 2-methoxy-ethanol / 20 °C / 3000.3 Torr View Scheme

: 9-amino-7-(dimethylamino)doxycycline hydrochloride

: tert-butylaminoacetic acid hydrochloride

: 220620-09-7
tigecycline

Conditions

Conditions	Yield
In water at 0 - 5℃; for 1h; Inert atmosphere;

: 220620-09-7
tigecycline

: 197654-04-9
tigecycline hydrochloride

Conditions

Conditions	Yield
Stage #1: tigecycline In acetone at 20℃; for 1.83333h; Stage #2: With hydrogenchloride In water; acetone at 20℃; for 5h; Product distribution / selectivity;	97%
Stage #1: tigecycline In acetonitrile at 20℃; for 1h; Stage #2: With hydrogenchloride In water; acetonitrile at 20℃; for 4 - 20h; Product distribution / selectivity;	88%
With hydrogenchloride In water at 20℃; for 92h; Product distribution / selectivity;	33%

: 220620-09-7
tigecycline

: C27H32N4O9

Conditions

Conditions	Yield
Stage #1: tigecycline With mercury(II) diacetate In N,N-dimethyl-formamide at 20℃; for 1.5h; Molecular sieve; Stage #2: With dipotassium hydrogenphosphate; water; edetate disodium In N,N-dimethyl-formamide at 0 - 5℃; for 0.833333h; pH=5.5;	94%

: 76-05-1
trifluoroacetic acid

: 220620-09-7
tigecycline

: C2HF3O2*C27H32N4O9

Conditions

Conditions	Yield
Stage #1: tigecycline With ethylenediaminetetraacetic acid; silver carbonate In dimethyl sulfoxide at 20℃; for 16h; Molecular sieve; Stage #2: With dipotassium hydrogenphosphate; water; edetate disodium In dimethyl sulfoxide; acetonitrile at 0 - 5℃; for 0.833333h; pH=5.5; Stage #3: trifluoroacetic acid HPLC;	83%

: 220620-09-7
tigecycline

: tigecycline dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In dichloromethane; acetonitrile at 20 - 70℃;

: 220620-09-7
tigecycline

: C26H32N4O7

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: mercury(II) diacetate / N,N-dimethyl-formamide / 1.5 h / 20 °C / Molecular sieve 1.2: 0.83 h / 0 - 5 °C / pH 5.5 2.1: edetate disodium / 30 h / 35 °C / pH 6.4 / aq. phosphate buffer View Scheme

: 220620-09-7
tigecycline

: C29H37N5O8

Conditions

Conditions	Yield
With mercury(II) diacetate In N,N-dimethyl-formamide at 20℃; for 1.5h; Molecular sieve;	580 mg

: calcium(II) chloride dihydrate

: 220620-09-7
tigecycline

: 3C29H39N5O8*2Ca(2+)

Conditions

Conditions	Yield
In aq. buffer at 25℃; pH=7.5;

: 10199-89-0
NBD chloride

: 220620-09-7
tigecycline

: C35H40N8O11

Conditions

Conditions	Yield
In aq. buffer at 75℃; for 0.25h; pH=9; pH-value; Solvent; Temperature;

: 220620-09-7
tigecycline

: C29H39N5O9

Conditions

Conditions	Yield
With oxygen; tetracycline destructase Tet(X4)-producing Escherichia coli JM109 strain pBAD24; NADPH at 37℃; for 3h; Enzymatic reaction;

Tigecycline Specification

1. Introduction of Tigecycline

Tigecycline, with its CAS NO.220620-09-7, is a kind of orange Powder. Its Synonyms are 2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)- ; Tygacil ; (4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide . Tigecycline is bacteriostatic and is a protein synthesis inhibitor by binding to the 30S ribosomal subunit of bacteria and thereby blocking entry of Aminoacyl-tRNA into the A site of the ribosome during prokaryotic translation.

2. Properties of Tigecycline

(1) XLogP3: -0.2 (2) H-Bond Donor: 7 (3) H-Bond Acceptor: 12
(4) Surface Tension: 80.036 dyne/cm (5) Density: 1.455 g/cm3 (6) Flash Point: 492.612 °C
(7) Enthalpy of Vaporization: 135.666 kJ/mol (8) Boiling Point: 890.922 °C at 760 mmHg

3. Structure descriptors of Tigecycline

IUPAC Name: (4S,4aS,5aR,12aR)-9-[[2-(tert-butylamino)acetyl]amino]-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,
6-tetrahydro-4H-tetracene-2-carboxamide

InChI: InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36-37,40,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1

InChIKey: SOVUOXKZCCAWOJ-HJYUBDRYSA-N

Canonical SMILES : CC(C)(C)NCC(=O)NC1=C(C2=C(CC3CC4C(C(=O)C(=C(C4(C(=O)C3=C2O)O)O)C(=O)N)N(C)C)C(=C1)N(C)C)OIsomeric SMILES: CC(C)(C)NCC(=O)NC1=C(C2=C(C[C@H]3C[C@H]4[C@@H](C(=O)C(=C([C@]4(C(=O)C3=
C2O)O)O)C(=O)N)N(C)C)C(=C1)N(C)C)O

4. Uses of Tigecycline

Tigecycline is active against many bacteria including Gram-positive bacteria, Gram-negative bacteria and anaerobes ,it also has activity against methicillin-resistant Staphylococcus aureus (MRSA) and multi-drug resistant strains of Acinetobacter baumannii. It may have no activity against Pseudomonas spp. or Proteus spp. The drug is licenced for the treatment of skin,soft tissue infections ,and intra-abdominal infections.

Product Name

Tigecycline

Synthetic route

Tigecycline Specification

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