4-amino-n-butyric acid
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 4-amino-n-butyric acid With phosphonic Acid; phosphorus trichloride In methoxybenzene at 60 - 105℃; for 5.66667 - 5.75h; Stage #2: With water In methoxybenzene at 110 - 115℃; for 5 - 6h; Reflux; | 90% |
Stage #1: 4-amino-n-butyric acid With phosphorus trichloride In methanesulfonic acid at 80 - 85℃; Stage #2: With water In methanesulfonic acid at 105℃; for 4h; | 88% |
Stage #1: 4-amino-n-butyric acid With phosphonic Acid; phosphorus trichloride In methanesulfonic acid at 65 - 70℃; for 18h; Stage #2: With water In methanesulfonic acid for 5h; Reflux; | 85% |
[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-1-hydroxy-1-phosphonobutyl]phosphonic acid
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With hydrazine hydrate In water at 20℃; for 0.5h; | 82% |
With hydrogenchloride In water for 5.5h; Reflux; |
2-pyrrolidinon
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 2-pyrrolidinon With methanesulfonic acid at 100 - 105℃; for 6h; Stage #2: With phosphorus trichloride at 75℃; for 8h; Stage #3: In water for 5h; Heating; | 72% |
1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
70% |
N-hydroxysuccinimide ester of 4-(tert-butoxycarbonylamino)butyric acid
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With tris(trimethylsilyl) phosphite In tetrahydrofuran at 50℃; for 72h; | 61% |
tetramethyl (4-phthalimido-1-hydroxybutylidene)bisphosphonate
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With hydrogenchloride for 10h; Heating; |
4-phthalimidobutyryl chloride
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With hydrogenchloride; methyl phosphite; phosphorous acid trimethyl ester 1.) 80 deg C, 8 h, 2.) reflux, 20 h; Yield given. Multistep reaction; |
sodium alendronate
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With hydrogenchloride; ethanol; water at 20 - 50℃; for 2h; |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With hydrogen bromide In water for 17h; Reflux; |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water for 17h; Reflux; |
4-amino-1-hydroxybutylidenebisphosphonic acid
tetra(n-butyl)ammonium hydroxide
Conditions | Yield |
---|---|
In water at 40℃; for 0.5h; | 100% |
In water at 20℃; for 2h; | 100% |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With anion-exchange column Amberlyst A26-OH In methanol; water at 20℃; for 1h; | 100% |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With anion-exchange column Amberlyst A26-OH In methanol; water at 20℃; for 1h; | 100% |
2,4,6-triamino-s-triazine
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With water pH=Ca. 6 - 8; Heating; | 99% |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 4-amino-1-hydroxybutylidenebisphosphonic acid; C29H23N5O6 With triethylamine In 1,4-dioxane; water at 25℃; Inert atmosphere; Stage #2: With sodium acetate; acetic acid In methanol at 80℃; for 1h; | 93.1% |
4-(N-maleimidomethyl)cyclohexane-1-carboxylic acid N-succinimidyl ester
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 20℃; pH=8 - 9; | 93% |
2,5-dioxopyrrolidin-1-yl pent-4-ynoate
4-amino-1-hydroxybutylidenebisphosphonic acid
1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid
Conditions | Yield |
---|---|
In water; acetonitrile at 20℃; for 12h; pH=7.0; | 90% |
With sodium hydroxide In water; acetonitrile at 0℃; for 18h; pH=7.2 - 7.4; Inert atmosphere; | 277 mg |
4-amino-1-hydroxybutylidenebisphosphonic acid
1-hydroxy-4-pent-4-ynamidobutane-1,1-diyldiphosphonic acid
Conditions | Yield |
---|---|
90% |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
In water for 4 - 5h; pH=4.2 - 4.8; Na+ Exchange resin AMBERLITE SR1L; Product distribution / selectivity; | 89.2% |
In water for 4 - 5h; pH=4.2 - 4.8; Na+ Exchange resin AMBERJET 1200; Product distribution / selectivity; | 89.9% |
4-{2-azatricyclo[10.4.0.04'9]hexadeca-1(12),4(9),5,7,13,15-hexaen-10-yn-2-yl}-4-oxobutanoic acid
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
In water; dimethyl sulfoxide pH=8.1; | 89% |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With lithium carbonate In water | 87% |
4-amino-1-hydroxybutylidenebisphosphonic acid
water
Conditions | Yield |
---|---|
With NaOH In water to an aq. soln. of I2Mo10-contg. compd. (0.417 mmol) was added a ligand (2.09 mmol); pH=5 (NaOH); stirring at 80°C for 30 min; cooling toroom temp.; powder was eliminated by centrifugation; addn. of RbCl (8.1 0 mmol); stirring for 1 h; the powder was filtered off, the soln. was left to evap. at room temp.; crystals were collected by filtration; elem. anal.; | 86% |
4-chloroquinazoline
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 4-chloroquinazoline; 4-amino-1-hydroxybutylidenebisphosphonic acid With potassium carbonate In water at 95℃; for 20h; Reflux; Stage #2: With hydrogenchloride In water at 5℃; for 24h; pH=1; | 83% |
3-thiophene carboxaldehyde
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 3-thiophene carboxaldehyde; 4-amino-1-hydroxybutylidenebisphosphonic acid With triethylamine In methanol at 65℃; for 1.5h; Stage #2: With tetramethylammonium borohydride In methanol at 65℃; Stage #3: With sodium hexaflorophosphate In methanol at 20℃; | 82% |
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With triethylamine In water; N,N-dimethyl-formamide at 20℃; for 0.166667h; | 80% |
2-chloroquinazoline
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 2-chloroquinazoline; 4-amino-1-hydroxybutylidenebisphosphonic acid With potassium carbonate In water at 90 - 180℃; for 25h; Reflux; Stage #2: With hydrogenchloride In water at 5℃; for 24h; pH=1; | 80% |
4-amino-1-hydroxybutylidenebisphosphonic acid
sodium alendronate
Conditions | Yield |
---|---|
With sodium carbonate In water for 3h; Heating; | 79% |
With sodium hydroxide In water at 0 - 5℃; for 3h; pH=4.3; | |
With sodium hydroxide In water at 30 - 70℃; |
6-maleimidohexanoic acid N-hydroxylsuccinimide ester
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 20℃; pH=8 - 9; | 79% |
4-amino-1-hydroxybutylidenebisphosphonic acid
ethylenediamine
Conditions | Yield |
---|---|
With water pH=Ca. 6 - 8; Heating; | 77% |
4-amino-1-hydroxybutylidenebisphosphonic acid
N-methyl-ethane-1,2-diamine
Conditions | Yield |
---|---|
With water pH=Ca. 6 - 8; Heating; | 76% |
2-chloropyrimidine
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
Stage #1: 2-chloropyrimidine; 4-amino-1-hydroxybutylidenebisphosphonic acid With potassium carbonate In water at 90 - 180℃; for 5h; Reflux; Stage #2: With hydrogenchloride In water at 5℃; pH=1; | 76% |
4-amino-1-hydroxybutylidenebisphosphonic acid
2-(triphenylmethylthio)ethanoic acid-N-hydroxysuccinimido ester
Conditions | Yield |
---|---|
Stage #1: 4-amino-1-hydroxybutylidenebisphosphonic acid With triethylamine In water for 0.0833333h; Stage #2: 2-(triphenylmethylthio)ethanoic acid-N-hydroxysuccinimido ester In water; N,N-dimethyl-formamide at 20℃; for 1h; | 76% |
Stage #1: 4-amino-1-hydroxybutylidenebisphosphonic acid With triethylamine In water for 0.0833333h; Stage #2: 2-(triphenylmethylthio)ethanoic acid-N-hydroxysuccinimido ester In water; N,N-dimethyl-formamide at 20℃; for 1h; | 76% |
4-amino-1-hydroxybutylidenebisphosphonic acid
N,N-diethylethylenediamine
Conditions | Yield |
---|---|
With water pH=Ca. 6 - 8; Heating; | 67% |
4-amino-1-hydroxybutylidenebisphosphonic acid
trans-1,2-Diaminocyclohexane
Conditions | Yield |
---|---|
With water pH=Ca. 6 - 8; Heating; | 66% |
1,3-di(aminomethyl)benzene
4-amino-1-hydroxybutylidenebisphosphonic acid
Conditions | Yield |
---|---|
With water pH=Ca. 6 - 8; Heating; | 62% |
The IUPAC name of Alendronate is (4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid. With the CAS registry number 66376-36-1, it is also named as Acide alendronique. The classification codes are Bone Density Conservation Agents; Reproductive Effect. It is white fine powder which is soluble in water, easily soluble in ethanol, and almost insoluble in chloroform. When heated to decomposition it emits toxic vapors of NOx and POx. Besides, this chemical is DBPA resorption inhibitors which is mainly used for the treatment of osteoporosis. Additionally, it should be sealed in the container and stored in the cool and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: -3.52; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -7.15; (4)ACD/LogD (pH 7.4): -7.92; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 8; (10)#H bond donors: 7; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 103.15 Å2; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 45.5 cm3; (15)Molar Volume: 134.1 cm3; (16)Surface Tension: 119.3 dyne/cm; (17)Enthalpy of Vaporization: 104.87 kJ/mol; (18)Vapour Pressure: 8.72E-18 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 249.016725; (21)MonoIsotopic Mass: 249.016725; (22)Topological Polar Surface Area: 161; (23)Heavy Atom Count: 14; (24)Complexity: 257.
Preparation of Alendronate: Adding 1mol 4-aminobutyric acid to 95 °C melting 1.5mol phosphoric acid. And then dropping 2mol phosphorus trihalides in 60min. When the reactants is hardening, heat 3h more. Then adding 300ml water to hydrolysis. After cooling, pouring into 1500ml methanol. Collecting the precipitate to get the product.
People can use the following data to convert to the molecule structure.
1. SMILES:O=P(O)(O)C(O)(CCCN)P(=O)(O)O
2. InChI:InChI=1/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)
3. InChIKey:OGSPWJRAVKPPFI-UHFFFAOYAU
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