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112101-81-2

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  • High Quality 99% Benzenesulfonamide,5-[(2R)-2-aminopropyl]-2-methoxy- 112101-81-2 ISO Manufacturer

    Cas No: 112101-81-2

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112101-81-2 Usage

General Description

R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide, also known as R-MAB-203, is a chemical compound with potential therapeutic uses. It is a potent and selective inhibitor of the enzyme carbonic anhydrase IX, which is overexpressed in various cancers. By inhibiting the activity of this enzyme, R-MAB-203 has the potential to suppress tumor growth and metastasis. This chemical has also shown promise in the treatment of hypoxic tumors, which are resistant to traditional chemotherapy and radiation therapy. Research on R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide is ongoing, and it may have future applications in cancer treatment and other medical fields.

Check Digit Verification of cas no

The CAS Registry Mumber 112101-81-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,2,1,0 and 1 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 112101-81:
(8*1)+(7*1)+(6*2)+(5*1)+(4*0)+(3*1)+(2*8)+(1*1)=52
52 % 10 = 2
So 112101-81-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H13NO4S/c1-7(12)5-8-3-4-9(15-2)10(6-8)16(11,13)14/h3-4,6H,5H2,1-2H3,(H2,11,13,14)

112101-81-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name R-(-)-5-(2-Amino-propyl)-2-methoxy-benzenesulfonamide

1.2 Other means of identification

Product number -
Other names R-(-)-5-2(2-AMinopropyl)-2-MethoxybenzenesulfonaMide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:112101-81-2 SDS

112101-81-2Synthetic route

(R)-2-(N-(trifluoroacetyl)arnino)-1-(4'-methoxy-3'-sulphamoyl)-phenylpropane
842130-16-9

(R)-2-(N-(trifluoroacetyl)arnino)-1-(4'-methoxy-3'-sulphamoyl)-phenylpropane

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With water; potassium carbonate In methanol for 8h; Heating / reflux;89%
(4R,5S)-5-(4-methoxy-3-sulfamoylphenyl)-4-methyloxazolidin-2-one
957777-99-0

(4R,5S)-5-(4-methoxy-3-sulfamoylphenyl)-4-methyloxazolidin-2-one

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 1h; atmospheric pressure;87%
C10H16N2O3S*C10H16O4S
906338-31-6

C10H16N2O3S*C10H16O4S

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With ammonia In water at 0 - 25℃; for 1h; pH=9.89 - 10.18; Product distribution / selectivity;82.06%
(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride

(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With potassium carbonate In water Product distribution / selectivity;82%
(R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide
112101-74-3

(R)-N-[1-(4-methoxy-3-sulfamoylphenylpropan-2-yl)]acetamide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
116091-64-6

5-[[(2R)-2-[(1R)-N-(1-methylbenzyl)]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
937018-25-2

(R)-5-(2-azidopropyl)-2-methoxybenzenesulfonamide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; for 1h;
(S)-5-(2-hydroxypropyl)-2-methoxybenzenesulfonamide
937018-24-1

(S)-5-(2-hydroxypropyl)-2-methoxybenzenesulfonamide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
937018-23-0

(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl acetate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
937018-21-8

(S)-1-(3-(chlorosulfonyl)-4-methoxyphenyl)propan-2-yl acetate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl methanesulfonate

(S)-1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl methanesulfonate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
131029-01-1

(S)-(+)-1-(4-methoxyphenyl)propan-2-ol

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
131029-02-2

(S)-1-(4-methoxyphenyl)propan-2-yl acetate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
123-11-5

4-methoxy-benzaldehyde

indenyl magnesium bromide

indenyl magnesium bromide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
111004-04-7

(1R,2S)-1-(4'-methoxyphenyl)-1,2-propanediol

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
863666-27-7

(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide D-tartrate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
112244-38-9

(+/-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide

A

(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide
119714-13-5

(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide

B

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With optical-resolution agent; diethylamine In methanol; ethanol at 40℃; Purification / work up; Optical-resolution column;A n/a
B n/a
(R)(+)-N-acetyl-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide

(R)(+)-N-acetyl-5-[(2-amino-2-methyl)ethyl]-2-methoxybenzenesulfonamide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
In hydrogenchloride
(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide dibenzoyl-D-tartrate
1161025-56-4

(R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide dibenzoyl-D-tartrate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With potassium carbonate In water at 20℃; for 1h;8 g
5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate
1210430-94-6

5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
116091-63-5

2-methoxy-5-(2-oxopropyl)benzenesulfonamide

A

(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide
119714-13-5

(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide

B

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
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
944395-49-7

2-methoxy-5-(2-hydroxyiminopropyl)benzenesulfonamide

A

(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide
119714-13-5

(S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide

B

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

Conditions
ConditionsYield
With hydrogen; 5%-palladium/activated carbon In methanol at 20℃; under 2206.72 Torr; for 8h;
N-benzenesulfonyl-N,N-bis(2-chloroethyl)amine
58023-19-1

N-benzenesulfonyl-N,N-bis(2-chloroethyl)amine

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

2-methoxy-5-{(2R)-2-[4-(benzenelsulfonyl)piperazin-1-yl]propyl}benzenesulfonamide

2-methoxy-5-{(2R)-2-[4-(benzenelsulfonyl)piperazin-1-yl]propyl}benzenesulfonamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine at 125 - 130℃; for 10h;90.83%
bromoacetic acid
79-08-3

bromoacetic acid

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

(R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

Conditions
ConditionsYield
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
35963-20-3

(R)-10-camphorsulfonic acid

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

C10H16N2O3S*C10H16O4S
906338-31-6

C10H16N2O3S*C10H16O4S

Conditions
ConditionsYield
In water; isopropyl alcohol at 0 - 4℃; for 1.5h; Product distribution / selectivity; Heating / reflux;85.65%
2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

(R)-2-bromo-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 5℃; Product distribution / selectivity;80%
methyl 2-ethoxyphenoxyacetate

methyl 2-ethoxyphenoxyacetate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide
133261-17-3

(R)-2-(2-ethoxyphenoxy)-N-[2-(4-methoxy-3-aminosulfonyl-phenyl)-1-methyl-ethyl]-acetamide

Conditions
ConditionsYield
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
169506-15-4

2-(2-ethyloxyphenoxy)ethyl methanesulfonate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(R)-tamsulosin
106133-20-4

(R)-tamsulosin

Conditions
ConditionsYield
With potassium hydrogencarbonate; potassium iodide In acetonitrile at 80℃; for 24h;74%
1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene
160969-00-6

1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide
1031281-18-1

(-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide

Conditions
ConditionsYield
In isopropyl alcohol for 16h; Reflux;69%
2-(o-ethoxyphenoxy)-ethyl bromide

2-(o-ethoxyphenoxy)-ethyl bromide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

5-((R)-2-{bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide
918867-88-6

5-((R)-2-{bis-[2-(2-ethoxyphenoxy)ethyl]amino}-propyl)-2-methoxybenzenesulfonamide

Conditions
ConditionsYield
With sodium oxalate In N,N-dimethyl-formamide at 80℃;64%
2-(2-ethyloxyphenoxy)ethyl methanesulfonate
169506-15-4

2-(2-ethyloxyphenoxy)ethyl methanesulfonate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

tamsulosin hydrochloride
106133-20-4

tamsulosin hydrochloride

Conditions
ConditionsYield
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;
2-(o-ethoxyphenoxy)-ethyl bromide

2-(o-ethoxyphenoxy)-ethyl bromide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(R)-tamsulosin
106133-20-4

(R)-tamsulosin

Conditions
ConditionsYield
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
1262059-05-1

1-(2-bromoethoxy)-2-isopropoxybenzene

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(-)-5-((2R)-2-{[2-(2-isopropoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide
1262059-02-8

(-)-5-((2R)-2-{[2-(2-isopropoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide

Conditions
ConditionsYield
In i-Amyl alcohol for 3h; Reflux;37%
2-(o-ethoxyphenoxy)-ethyl bromide

2-(o-ethoxyphenoxy)-ethyl bromide

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

tamsulosin hydrochloride
106133-20-4

tamsulosin hydrochloride

Conditions
ConditionsYield
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
154582-47-5

1-(benzyloxy)-2-(2-bromoethoxy)benzene

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(-)-5-[(2R)-2-({2-[2-(benzyloxy)phenoxy]ethyl}amino)propyl]-2-methoxybenzenesulfonamide
1262059-03-9

(-)-5-[(2R)-2-({2-[2-(benzyloxy)phenoxy]ethyl}amino)propyl]-2-methoxybenzenesulfonamide

Conditions
ConditionsYield
In i-Amyl alcohol for 3h; Reflux;25%
2-[2-(2,2,2-trifluoroethoxy)-phenoxy]ethyl 4-methylbenzenesulfonate
459868-80-5

2-[2-(2,2,2-trifluoroethoxy)-phenoxy]ethyl 4-methylbenzenesulfonate

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

(-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide
1031281-18-1

(-)-2-Methoxy-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]benzenesulfonamide

Conditions
ConditionsYield
In i-Amyl alcohol for 3h; Reflux;4%
2-chloro-6,7-dimethoxyquinazolin-4-amine
23680-84-4

2-chloro-6,7-dimethoxyquinazolin-4-amine

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

5-[(R)-2-(4-Amino-6,7-dimethoxy-quinazolin-2-ylamino)-propyl]-2-methoxy-benzenesulfonamide

5-[(R)-2-(4-Amino-6,7-dimethoxy-quinazolin-2-ylamino)-propyl]-2-methoxy-benzenesulfonamide

Conditions
ConditionsYield
In i-Amyl alcohol for 5h; Heating;
2-(2-ethoxyphenoxy)acetaldehyde
103181-55-1

2-(2-ethoxyphenoxy)acetaldehyde

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide
112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

5-{2-[2-(2-ethoxy-phenoxy)-ethylideneamino]-propyl}-2-methoxy-benzenesulfonamide

5-{2-[2-(2-ethoxy-phenoxy)-ethylideneamino]-propyl}-2-methoxy-benzenesulfonamide

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;

112101-81-2Relevant articles and documents

NOVEL PROCESS FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE 2-METHOXY-5-[(2R)-2-(4-ALKYLPIPERAZIN-L-YL)PROPYL]-BENZENESULFONAMIDE

-

Page/Page column 7-8, (2012/08/08)

Where R is C1-C3 alkyl, alkenyl A novel process for synthesis of compound of Formula 1 comprising steroselective catalytic reduction of compound of Formula IV under hydrogen gas pressure to obtain an intermediate compound of Formula II, which on coupling in presence of coupling agent and base in presence of organic solvent to obtain compound of Formula X, Formula X on reacting with deprotecting agent in presence of organic solvent results in formation of compound of Formula XI, condensation of Formula XI with alkyl halide results in formation of compound of Formula I.

Improved process for the preparation of tamsulosin hydrochloride

Reddy, A. Veera,Bhaskara Rao, S. Udaya,Narasimha, G. Lakshmi,Dubey

experimental part, p. 1451 - 1456 (2009/09/25)

Ellman's sulfinamide reagent is used in asymmetric synthesis of Tamsulosin hydrochloride. The enantiomeric ratio achieved is 87:13. The crystallization of the same with dibenzoyl tartarate afforded the product 2 with 99.5% ee.

Assymetric formal synthesis of (-)-formoterol and (-)-tamsulosin

Kim, Yongeun,Kang, Lae-Sung,Ha, Hyun-Joon,Ko, Seung Whan,Lee, Won Koo

, p. 2243 - 2248 (2008/09/17)

Biologically important (2R)-2-amino-3-phenylpropanes consisted in commercial drugs including (R,R)-formoterol, and (R)-tamsulosin were prepared from chiral (2R)-aziridine-2-carboxylate without any chromatographic separation. Key reactions include regio- and stereoselective ring opening reaction of aziridin-2-yl-phenylmethanol and subsequent cyclization toward enantiopure 4,5-disubastitued oxazolidin-2-ones as synthetic intermediates.

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