(R)-2-(N-(trifluoroacetyl)arnino)-1-(4'-methoxy-3'-sulphamoyl)-phenylpropane
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With water; potassium carbonate In methanol for 8h; Heating / reflux; | 89% |
(4R,5S)-5-(4-methoxy-3-sulfamoylphenyl)-4-methyloxazolidin-2-one
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 1h; atmospheric pressure; | 87% |
C10H16N2O3S*C10H16O4S
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With ammonia In water at 0 - 25℃; for 1h; pH=9.89 - 10.18; Product distribution / selectivity; | 82.06% |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With potassium carbonate In water Product distribution / selectivity; | 82% |
(R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Stage #1: (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide With hydrogenchloride; water for 16 - 18h; Heating / reflux; Stage #2: With sodium carbonate In water for 0.5h; pH=~ 10; Product distribution / selectivity; | 80% |
Stage #1: (R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide With hydrogenchloride; water for 18h; Heating / reflux; Stage #2: With potassium carbonate In water Product distribution / selectivity; | 80% |
5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Stage #1: 5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybensulfonamide hydrochloride; pyrographite In methanol at 20℃; for 0.5h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol at 60 - 65℃; under 2942.29 - 3677.86 Torr; Stage #3: With ammonia In water | 80% |
(R)-5-(2-azidopropyl)-2-methoxybenzenesulfonamide
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 1h; |
(S)-5-(2-hydroxypropyl)-2-methoxybenzenesulfonamide
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / pyridine / 2 h / 20 °C 2: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 3: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl acetate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 91 percent / KOH / methanol 2: 88 percent / pyridine / 2 h / 20 °C 3: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 4: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
(S)-1-(3-(chlorosulfonyl)-4-methoxyphenyl)propan-2-yl acetate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 2: 91 percent / KOH / methanol 3: 88 percent / pyridine / 2 h / 20 °C 4: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 5: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 2: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
(S)-(+)-1-(4-methoxyphenyl)propan-2-ol
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 90 percent / pyridine 2: 85 percent / chlorosulfonic acid / 1 h / 0 °C 3: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 4: 91 percent / KOH / methanol 5: 88 percent / pyridine / 2 h / 20 °C 6: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 7: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
(S)-1-(4-methoxyphenyl)propan-2-yl acetate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 85 percent / chlorosulfonic acid / 1 h / 0 °C 2: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 3: 91 percent / KOH / methanol 4: 88 percent / pyridine / 2 h / 20 °C 5: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 6: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
4-methoxy-benzaldehyde
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 21 percent / glucose / baker's yeast / H2O / 72 h / 20 °C 2: 86 percent / H2; HClO4 / Pd/C / ethanol / 20 °C / atmospheric pressure 3: 90 percent / pyridine 4: 85 percent / chlorosulfonic acid / 1 h / 0 °C 5: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 6: 91 percent / KOH / methanol 7: 88 percent / pyridine / 2 h / 20 °C 8: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 9: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
(1R,2S)-1-(4'-methoxyphenyl)-1,2-propanediol
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 86 percent / H2; HClO4 / Pd/C / ethanol / 20 °C / atmospheric pressure 2: 90 percent / pyridine 3: 85 percent / chlorosulfonic acid / 1 h / 0 °C 4: 79 percent / aq. ammonia / tetrahydrofuran / 1 h / 20 °C 5: 91 percent / KOH / methanol 6: 88 percent / pyridine / 2 h / 20 °C 7: 63 percent / sodium azide / dimethylformamide / 2 h / 40 °C 8: H2 / Pd/C / ethanol / 1 h / 20 °C View Scheme |
(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide D-tartrate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 1h; pH=9.5 - 10; | |
With sodium hydroxide In water at 20℃; for 1h; pH=9.5 - 10; | |
With sodium hydroxide In water at 25 - 30℃; for 1h; pH=9.5 - 10.0; | n/a |
(+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide
A
(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide
B
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With optical-resolution agent; diethylamine In methanol; ethanol at 40℃; Purification / work up; Optical-resolution column; | A n/a B n/a |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
In hydrogenchloride |
(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide dibenzoyl-D-tartrate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With potassium carbonate In water at 20℃; for 1h; | 8 g |
5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With potassium carbonate In water at 20℃; for 3h; | 0.45 g |
With hydrogenchloride In water; isopropyl alcohol at 45 - 50℃; for 1h; pH=2 - 3; |
2-methoxy-5-(2-oxopropyl)benzenesulfonamide
A
(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide
B
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride / methanol / 5 h / 20 °C 2: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 20 °C / 2206.72 Torr View Scheme |
2-methoxy-5-(2-hydroxyiminopropyl)benzenesulfonamide
A
(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide
B
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With hydrogen; 5%-palladium/activated carbon In methanol at 20℃; under 2206.72 Torr; for 8h; |
N-benzenesulfonyl-N,N-bis(2-chloroethyl)amine
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine at 125 - 130℃; for 10h; | 90.83% |
bromoacetic acid
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
Stage #1: bromoacetic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at -45 - -40℃; for 4h; Stage #2: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide In dichloromethane at -45 - -40℃; for 1.5h; Product distribution / selectivity; | 89.2% |
(R)-10-camphorsulfonic acid
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
C10H16N2O3S*C10H16O4S
Conditions | Yield |
---|---|
In water; isopropyl alcohol at 0 - 4℃; for 1.5h; Product distribution / selectivity; Heating / reflux; | 85.65% |
2-Bromoacetyl bromide
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 5℃; Product distribution / selectivity; | 80% |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide
Conditions | Yield |
---|---|
Stage #1: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With diisobutylaluminium hydride In tetrahydrofuran at 0 - 25℃; for 1.08333h; Stage #2: methyl 2-ethoxyphenoxyacetate In tetrahydrofuran; toluene at 20 - 25℃; for 16h; | 77% |
2-(2-ethyloxyphenoxy)ethyl methanesulfonate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(R)-tamsulosin
Conditions | Yield |
---|---|
With potassium hydrogencarbonate; potassium iodide In acetonitrile at 80℃; for 24h; | 74% |
1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide
Conditions | Yield |
---|---|
In isopropyl alcohol for 16h; Reflux; | 69% |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
5-((R)-2-{bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide
Conditions | Yield |
---|---|
With sodium oxalate In N,N-dimethyl-formamide at 80℃; | 64% |
2-(2-ethyloxyphenoxy)ethyl methanesulfonate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
tamsulosin hydrochloride
Conditions | Yield |
---|---|
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With sodium hydrogencarbonate; potassium iodide In DMF (N,N-dimethyl-formamide) at 55 - 65℃; for 11h; Stage #2: With hydrogenchloride In ethanol pH=2; | 56.9% |
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With calcium oxide In 2-methyl-propan-1-ol at 80 - 85℃; for 25h; Stage #2: With hydrogenchloride In 2-methyl-propan-1-ol; water at 60 - 65℃; pH=1.0; Product distribution / selectivity; | |
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With calcium oxide In ethanol at 78 - 80℃; for 35h; Stage #2: With hydrogenchloride In ethanol; water at 60 - 65℃; pH=1.0; Product distribution / selectivity; | |
Stage #1: 2-(2-ethyloxyphenoxy)ethyl methanesulfonate; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With calcium oxide In 2-methyl-propan-1-ol at 80 - 85℃; for 25h; Stage #2: With hydrogenchloride In 2-methyl-propan-1-ol; water at 60 - 65℃; pH=1.0; Product distribution / selectivity; |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(R)-tamsulosin
Conditions | Yield |
---|---|
With sodium carbonate In DMF (N,N-dimethyl-formamide) at 70℃; for 5h; | 50% |
Stage #1: 2-(o-ethoxyphenoxy)-ethyl bromide; 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide In methanol at 25 - 35℃; for 48h; Heating / reflux; Stage #2: With potassium carbonate In dichloromethane; water | |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 100℃; for 1.5h; Product distribution / selectivity; |
1-(2-bromoethoxy)-2-isopropoxybenzene
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(-)-5-((2R)-2-{[2-(2-isopropoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide
Conditions | Yield |
---|---|
In i-Amyl alcohol for 3h; Reflux; | 37% |
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
tamsulosin hydrochloride
Conditions | Yield |
---|---|
In ethanol Heating / reflux; | 32% |
Stage #1: 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide With sodium hydrogencarbonate In triethyl phosphite Stage #2: 2-(o-ethoxyphenoxy)-ethyl bromide In water; triethyl phosphite for 6h; Heating / reflux; Stage #3: With hydrogenchloride; ammonia Product distribution / selectivity; more than 3 stages; | 30.36% |
In ethanol for 16h; Heating / reflux; |
1-(benzyloxy)-2-(2-bromoethoxy)benzene
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(-)-5-[(2R)-2-({2-[2-(benzyloxy)phenoxy]ethyl}amino)propyl]-2-methoxybenzenesulfonamide
Conditions | Yield |
---|---|
In i-Amyl alcohol for 3h; Reflux; | 25% |
2-[2-(2,2,2-trifluoroethoxy)-phenoxy]ethyl 4-methylbenzenesulfonate
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
(-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide
Conditions | Yield |
---|---|
In i-Amyl alcohol for 3h; Reflux; | 4% |
2-chloro-6,7-dimethoxyquinazolin-4-amine
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
In i-Amyl alcohol for 5h; Heating; |
2-(2-ethoxyphenoxy)acetaldehyde
5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
Conditions | Yield |
---|---|
In ethanol at 20℃; for 1h; |
The CAS register number of R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide is 112101-81-2. It also can be called as R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide and the systematic name about this chemical is 5-[(2S)-2-aminopropyl]-2-methoxybenzenesulfonamide. The molecular formula about this chemical is C10H16N2O3S and the molecular weight is 244.31. It belongs to the Tamsulosin.
Physical properties about R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide are: (1)(1)ACD/LogP: -0.26; (2)ACD/LogD (pH 5.5): -3; (3)ACD/LogD (pH 7.4): -2; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 103.79Å2; (12)Index of Refraction: 1.557; (13)Molar Refractivity: 63.043 cm3; (14)Molar Volume: 195.762 cm3; (15)Polarizability: 24.992x10-24cm3; (16)Surface Tension: 48.927 dyne/cm; (17)Enthalpy of Vaporization: 70.351 kJ/mol; (18)Boiling Point: 445.507 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: O=S(=O)(c1cc(ccc1OC)C[C@@H](N)C)N
(2)InChI: InChI=1/C10H16N2O3S/c1-7(11)5-8-3-4-9(15-2)10(6-8)16(12,13)14/h3-4,6-7H,5,11H2,1-2H3,(H2,12,13,14)/t7-/m0/s1
(3)InChIKey: IORITYIZDHJCGT-ZETCQYMHBG
(4)Std. InChI: InChI=1S/C10H16N2O3S/c1-7(11)5-8-3-4-9(15-2)10(6-8)16(12,13)14/h3-4,6-7H,5,11H2,1-2H3,(H2,12,13,14)/t7-/m0/s1
(5)Std. InChIKey: IORITYIZDHJCGT-ZETCQYMHSA-N
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