133909-99-6

Basic information

• Product Name: Trityl losartan
• Synonyms: 2-BUTYL-4-CHLORO-1-[[2'-[2-(TRIPHENYLMETHYL)-TETRAZOL-5-YL]-[1,1'-BIPHENYL]-4-YL]METHYL]-1H-IMIDAZOLE-5-METHANOL;2-BUTYL-4-CHLORO-1-[2'-(2-TRITYL-2H-TETRAZOLE-5-YL)BIPHENYL-4-YL-METHYL-1H-IMIDAZOLE-5-YL-METHANOL;(2-butyl-4-chloro-1-((2`-(1-trityl-1H-tetrazol-5-yl)biphenyl-1-4-yl)methyl)-1H-i;(2-Butyl-4-Chloro-1-((2'-(1-Trityl-1h-Tetrazole-5-Yl)Biphenyl-4-Yl)Methyl)-1h-Imidazol-5-Yl)Methanol;Trithyl Losartan;2-butyl-4-chloro-1-[2'(2-trityl-2h-tetrazol-5-yl)biphenyl-4-ylmethyl]-1h-imidazol-5-ylmethanol;TRIPHENYL LOSARTAN;2-butyl-4-chloro-4,5-dihydro-5-hydroxymethyl-1-[2'-(2-triphenylmethyl-1,2,3,4-2H-tetrazol-5-yl)-1,1'-biphenyl-4-methyl]-1H-imidazole
• CAS NO: 133909-99-6
• Molecular Formula: C₄₁H₃₇ClN₆O
• Molecular Weight: 665.23
• EINECS: 412-420-5
• Mol File: 133909-99-6.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 856.6 °C at 760 mmHg
• Flash Point: 471.9 °C
• Appearance: /
• Density: 1.22 g/cm³
• PKA: 13.66±0.10(Predicted)
• CAS DataBase Reference: Trityl losartan(CAS DataBase Reference)
• NIST Chemistry Reference: Trityl losartan(133909-99-6)
• EPA Substance Registry System: Trityl losartan(133909-99-6)

Safety Data

• Statements: 53
• Safety Statements: 61
• Hazardous Substances Data: 133909-99-6(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Intermediate in the preparation of Losartan impurities

Uses

N-Trityl Losartan (Losartan EP Impurity H) is an intermediate in the preparation of Losartan impurities

Synthetic route

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde; N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole With potassium carbonate In N,N-dimethyl-formamide at 20 - 22℃; for 3h; Stage #2: With sodium tetrahydroborate In water; N,N-dimethyl-formamide at 48 - 52℃; for 3.08333h;	99.2%
With potassium carbonate In N,N-dimethyl acetamide
With potassium carbonate In N,N-dimethyl acetamide

trityl chloride (76-83-5) + cozaar (124750-99-8) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h;	91%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 10h;	80%

n-Butyl chloride (109-69-3) + 2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde (133910-00-6) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With sodium borohydrid In water; ethyl acetate	72%
With sodium borohydrid In water; ethyl acetate	72%

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde (133910-00-6) + 3-<3,4-bis(benzyloxy)phenyl>-1-aminopropane (99281-96-6) → [3-(3,4-bis-benzyloxy-phenyl)propyl](2-n-butyl-5-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl)amine (1370339-88-0) + 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Stage #1: 2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde; 3-<3,4-bis(benzyloxy)phenyl>-1-aminopropane With magnesium sulfate In dichloromethane at 20℃; for 17h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 20℃; for 4h; Inert atmosphere;	A 34% B 40%

n-Butyl chloride (109-69-3) + 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 5-(4'-Methanesulfonyloxymethyl-1,1'-biphenyl-2-yl)-2-triphenylmethyl-2H-tetrazole (143722-28-5) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With sodium borohydrid In water; ethyl acetate; acetone	28%
With sodium borohydrid In water; ethyl acetate; acetone	28%

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) + N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) + {2-Butyl-5-chloro-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazol-4-yl}-methanol

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Product distribution; Ambient temperature; various ratios of reagents;
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;

trityl chloride (76-83-5) + 2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole (114772-55-3) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Yield given. Multistep reaction;

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde (133910-00-6) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With sodium tetrahydroborate In dichloromethane at 25℃; for 24h; Yield given;

2-trityl-5-phenyl-2H-tetrazole (87268-78-8) + 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-1H-imidazole-5-methanol (151012-31-6) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Yield given. Multistep reaction;

2-(2'-Triphenylmethyl-2'H-tetrazol-5'-yl)-phenylboronic acid (143722-25-2) + 2-n-Butyl-4-chloro-1-(4-bromobenzyl)-1H-imidazole-5-methanol (151012-31-6) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 75℃;
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 75℃; Mechanism; coupling rate effects of changing the initial composition; coupling rate effect of isomeric impurity of the aryl bromide;

2-n-butyl-4-chloro-5-hydroxymethylimidazole (79047-41-9) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / N,N-dimethyl-acetamide View Scheme
Multi-step reaction with 3 steps 1: 77 percent / 1.0 N aq. ceric ammonium nitrate / acetic acid / 3 h / 25 °C 2: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 3: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

trityl chloride (76-83-5) + diphenylchloromethane (?) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 0.5 h View Scheme

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) K2CO3, 2.) NaBH4 / 1.) dimethylacetamide, -10 deg C, 2 h; room temp., 2 h, 2.) MeOH, room temp., 1 h View Scheme
Multi-step reaction with 2 steps 1: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 2: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

1-bromomethyl-4-bromobenzene (589-15-1) + sodium-<4-nitro benzoate> → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / N,N-dimethyl-acetamide View Scheme
Multi-step reaction with 2 steps 1: 1.) K2CO3, 2.) NaBH4 / 1.) dimethylacetamide, -10 deg C, 2 h; room temp., 2 h, 2.) MeOH, room temp., 1 h View Scheme

5-phenyl-2H-1,2,3,4-tetrazole (18039-42-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 0.5 h View Scheme

2-(2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (57598-33-1) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 5 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 4: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme
Multi-step reaction with 6 steps 1: tetrahydrofuran / 2 h / 20 °C 2: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 3: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 4: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 5: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 6: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

2-Cyano-4'-methylbiphenyl (114772-53-1) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 2: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme
Multi-step reaction with 4 steps 1: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 2: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 4: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

4'-(bromomethyl)-1,1'-biphenyl-2-carbonitrile (114772-54-2) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme

N-(2-hydroxy-1,1-dimethyl)-2-methoxybenzamide (74201-13-1) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 6 steps 1: thionyl chloride / 1 h / 25 °C 2: tetrahydrofuran / 2 h / 20 °C 3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 4: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 5: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme
Multi-step reaction with 7 steps 1: thionyl chloride / 1 h / 25 °C 2: tetrahydrofuran / 2 h / 20 °C 3: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 4: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 5: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 6: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 7: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

4,4-dimethyl-2-(4'-methyl-biphenyl-2-yl)-4,5-dihydrooxazole (84392-32-5) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 2: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 3: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme
Multi-step reaction with 5 steps 1: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 2: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 3: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 4: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 5: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

N-(trityl)-5-[4΄-(methyl)biphenyl-2-yl]-2H-tetrazole (133909-97-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 2: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 3: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

N-(triphenylmethyl)-5-<4'-(bromomethyl)biphenyl-2-yl>tetrazole (133051-88-4) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 2: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

2-Methoxybenzoic acid (579-75-9) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 8 steps 1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH2Cl2 / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C 4: tetrahydrofuran / 2 h / 20 °C 5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 6: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 7: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme
Multi-step reaction with 9 steps 1: 95 percent / thionyl chloride / 18 h / 20 °C 2: CH2Cl2 / 2 h / 20 °C 3: thionyl chloride / 1 h / 25 °C 4: tetrahydrofuran / 2 h / 20 °C 5: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 6: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 7: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 8: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 9: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

2-Methoxybenzoyl chloride (21615-34-9) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 7 steps 1: CH2Cl2 / 2 h / 20 °C 2: thionyl chloride / 1 h / 25 °C 3: tetrahydrofuran / 2 h / 20 °C 4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 5: N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 6: 1.) sodium methoxide / 1.) DMF, 25 deg C, 0.25 h, 2.) DMF, 40 deg C, 4 h View Scheme
Multi-step reaction with 8 steps 1: CH2Cl2 / 2 h / 20 °C 2: thionyl chloride / 1 h / 25 °C 3: tetrahydrofuran / 2 h / 20 °C 4: 96 percent / pyridine, phosphorus oxychloride / 3 h / 100 °C 5: 1.) tributyltin chloride, sodium azide, 2.) 10 N aq. sodium hydroxide / 1.) toluene, reflux, 70 h, 20 deg C, 3 h 6: 92 percent / N-bromosuccinimide, dibenzoyl peroxide / CCl4 / 3 h / Heating 7: 49 percent / potassium carbonate / dimethylformamide / 24 h / 25 °C 8: sodium borohydride / CH2Cl2 / 24 h / 25 °C View Scheme

1H-imidazole (288-32-4) + 2-(2'-Triphenylmethyl-2'H-tetrazol-5'-yl)-phenylboronic acid (143722-25-2) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With potassium carbonate In tetrahydrofuran; formaldehyde diethyl acetal; water	15.5 g (93%)
With tributylphosphine; potassium carbonate In tetrahydrofuran; formaldehyde diethyl acetal; water	15.5 g (93%)
With potassium carbonate In tetrahydrofuran; formaldehyde diethyl acetal; water

2-methylpropyl acetate (110-19-0) + pyrographite (7440-44-0) + 2-(2'-Triphenylmethyl-2'H-tetrazol-5'-yl)-phenylboronic acid (143722-25-2) + 2-n-Butyl-4-chloro-1-p-bromobenzyl-1H-imidazole-5-carboxaldehyde (143722-29-6) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
With sodium borohydrid; nitrogen; tetrabutylammomium bromide; magnesium sulfate; potassium carbonate; thiourea; triphenylphosphine; tris-(dibenzylideneacetone)dipalladium(0) In water; toluene
With sodium borohydrid; nitrogen; tetrabutylammomium bromide; magnesium sulfate; potassium carbonate; thiourea; triphenylphosphine; tris-(dibenzylideneacetone)dipalladium(0) In water; toluene

4-bromobenzenemethanol (873-75-6) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: nitrogen / tetrakis(triphenylphosphine)palladium (0) / toluene 2: potassium carbonate / N,N-dimethyl acetamide 3: sodium borohydrid / water; ethyl acetate; acetone View Scheme

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) + 1-bromomethyl-4-bromobenzene (589-15-1) → 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl acetamide; water; toluene 2: sodium borohydrid; nitrogen; tetrabutylammomium bromide; magnesium sulfate; potassium carbonate; thiourea; triphenylphosphine / tris-(dibenzylideneacetone)dipalladium(0) / water; toluene View Scheme

2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → 2-n-butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]imidazole (114798-26-4)

Conditions	Yield
With sulfuric acid In water; acetonitrile for 0.583333h; Ambient temperature;	95%
Stage #1: 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol With hydrogenchloride In water; acetonitrile at 18 - 20℃; for 5h; Stage #2: With sodium hydroxide In water pH=12.3 - 12.7;	90.5%
With hydrogenchloride In dichloromethane; water at 25 - 35℃; for 1 - 1.5h; Product distribution / selectivity;

2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → lorsartan (114798-26-4)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 25℃; for 4h;	89%

2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → cozaar (124750-99-8)

Conditions	Yield
With potassium carbonate In methanol for 12h; Product distribution / selectivity; Heating / reflux;	82%
With potassium tert-butylate In methanol; isopropyl alcohol for 9h; Product distribution / selectivity; Heating / reflux;	81%
With potassium tert-butylate In methanol for 8h; Heating / reflux;	78%
With potassium tert-butylate In methanol for 8h; Heating / reflux;	78%
With potassium tert-butylate In methanol; tert-butyl alcohol for 9h; Product distribution / selectivity; Heating / reflux;	78%

3,5-di-tert-butyl-4-hydroxyphenyl acetic acid (1611-03-6) + 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → (3,5-di-tert-butyl-4-hydroxyphenyl)-acetic acid 2-butyl-5-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-imidazol-4-yl methyl ester (1195777-21-9)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In diethyl ether at 20℃; for 12h; Mitsunobu reaction; Inert atmosphere;	63%

3-(3,4-bis(benzyloxy)phenyl)propanoic acid (93559-04-7) + 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → C64H57ClN6O4 (1195777-19-5)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In diethyl ether at 20℃; for 12h; Mitsunobu reaction; Inert atmosphere;	63%

4-(benzyloxy)-3,5-dimethoxybenzoic acid (14588-60-4) + 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → 4-benzyloxy-3,5-dimethoxybenzoic acid 5-chloro-2-butyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-yl methyl ester (1195777-18-4)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In diethyl ether at 20℃; for 12h; Mitsunobu reaction; Inert atmosphere;	62%

dodecyl mesylate (51323-71-8) + 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → 5-[4'-(2-butyl-4-chloro-5-dodecyloxymethylimidazol-1-ylmethyl)biphenyl-2-yl]-2-trityl-2H-tetrazole

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: dodecyl mesylate In tetrahydrofuran for 24h; Inert atmosphere; Reflux;	45%

2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) + 6-tert-butyl(dimethyl)silyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid (716320-66-0) → 6-(tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethylchroman-2-carboxylic acid 2-butyl-5-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-midazol-4-yl methyl ester (1195777-20-8)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In diethyl ether at 20℃; for 12h; Mitsunobu reaction; Inert atmosphere;	42%

4-hydroxy-benzaldehyde (123-08-0) + 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol (133909-99-6) → 4-{2-butyl-5-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethoxy}benzaldehyde

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 18h; Mitsunobu Displacement; Cooling with ice;	35%

Upstream product

• 133909-97-4 4-Methyl-[2'-(2-Trityl-2H-Tetr 
• 133909-96-3 3-(4-Methylphenyl)benzonitrile 
• 133909-68-9 2H-Pyran-3-ol,tetrahydro-6-methyl-2-(1-methylethyl)-,(2alpha,3bta,6alpha)-(9CI) 
• 133909-63-4 2-Butanone,4-[3-(1-methylethyl)oxiranyl]-,trans-(9CI) 
• 133908-85-7 L-Ribono-1,4-lactone 
• 133908-64-2 1,4:3,6-dianhydro-2-O-{[5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridin-3-yl]carbonyl}hexitol 
• 133908-22-2 D-ERYTHRO-PENTOFURANOSIDE, METHYL 3-AZIDO-2,3-DIDEOXY-5-O-[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]- 
• 133908-08-4 2H-Pyrrol-2-one,1,5-dihydro-4-methoxy-5-(1-methylethyl)-,(S)-(9CI) 
• 133908-07-3 4A,23,24-TRIMETHYLCHOLESTANE 
• 13390-78-8 azacyclotridecan-2-one, sodium salt 
• 133907-77-4 Pyrazino[2,3-b]pyrazine, decahydro-2,7-dimethyl-, (2-alpha-,4a-ba-,7-alpha-,8a-alpha-)- (9CI) 
• 133907-76-3 Pyrazino[2,3-b]pyrazine, decahydro-2,6-dimethyl-, (2-alpha-,4a-alpha-,6-alpha-,8a-ba-)- (9CI) 
• 133907-73-0 Pyrazino[2,3-b]pyrazine, decahydro-2,6-dimethyl-, (2-alpha-,4a-alpha-,6-ba-,8a-ba-)- (9CI) 
• 133906-92-0 Leucine, N-(1-oxohexyl)- 

Downstream Products

• 133910-00-6 N-Trityl Losartan Carboxaldehyde 
• 133910-11-9 22-(3-(dimethylhydroxymethyl)phenyl)-23,24,25,26,27-pentanor-1-hydroxyvitamin D3 
• 133910-12-0 3-(T-BUTYLDIMETHYLSILOXY)IODOBENZENE 
• 133911-19-0 2-Butanone, 3-hydroxy-, O-methyloxime, (Z)- (9CI) 
• 13391-15-6 N,N-bis(2,3-epoxypropyl)cyclohexylamine 
• 1339121-92-4 3-Ethoxypyrazine-2-carboxylic acid 
• 13391-27-0 5-METHOXY-2-METHYLBENZOFURAN 
• 13391-28-1 5-Methoxybenzofuran 
• 13391-31-6 4-methoxy-2-propylphenol 
• 13391-33-8 5-methoxy-2-methyl-2,3,4,7-tetrahydro-1-benzofuran 
• 13391-34-9 5-methoxy-2,3,4,7-tetrahydro-1-benzofuran 
• 13391-35-0 4-ALLYLOXYANISOLE 
• 1339138-20-3 1-ACETAMIDO-3-AMINO-2-METHYLPROPANE 
• 13391-38-3 1-(α-Chlorobenzyl)-4-bromobenzene 

Recommend Products

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