16652-64-5

Basic information

• Product Name: H-TYR(BZL)-OH
• Synonyms: (2S)-2-aMino-3-[4-(benzyloxy)phenyl]propanoic acid;(S)-2-AMino-3-(4-benzyloxyphenyl)propanoic;O-Benzyl-L-tyrosine >=99.0% (NT);L-Tyr(Bzl)-OH;(S)-2-AMINO-3-(4'-BENZYLOXYPHENYL)PROPANOIC ACID;O-BENZYL-L-TYR;O-BENZYL-L-TYROSINE;TYROSINE(BZL)-OH
• CAS NO: 16652-64-5
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.31
• EINECS: 240-699-1
• Product Categories: API intermediates;Amino Acids;Tyrosine [Tyr, Y];Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 16652-64-5.mol
• Article Data: 15

Chemical Properties

• Melting Point: 259 °C (dec.)(lit.)
• Boiling Point: 414.4°C (rough estimate)
• Flash Point: 229.7 °C
• Appearance: White/Powder
• Density: 1.1111 (rough estimate)
• Vapor Pressure: 4.12E-09mmHg at 25°C
• Refractive Index: -10 ° (C=1, 80% AcOH)
• Storage Temp.: Store at RT.
• PKA: 2.24±0.10(Predicted)
• BRN: 2659642
• CAS DataBase Reference: H-TYR(BZL)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-TYR(BZL)-OH(16652-64-5)
• EPA Substance Registry System: H-TYR(BZL)-OH(16652-64-5)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 16652-64-5(Hazardous Substances Data)

Usage

Chemical Properties

Crystalline

Uses

O-Benzyl-L-tyrosine is a substrate for aminotransferases PAT3.

InChI:InChI=1/C16H17NO3/c17-15(16(18)19)10-12-6-8-14(9-7-12)20-11-13-4-2-1-3-5-13/h1-9,15H,10-11,17H2,(H,18,19)/t15-/m1/s1

Synthetic route

O-benzyl-L-tyrosine coper complex → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
With sodium sulfide In water at 25 - 30℃; for 0.166667h;	93%

O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3) → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
With ammonia; hydrogen; palladium on activated charcoal In methanol for 0.5h; Ambient temperature;	89%
With hydrogenchloride In diethyl ether Hydrolysis;
With trifluoroacetic acid at 20℃; for 0.25h;

Oϖ-Bzl-L-Tur/copper complex → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
With N,N-Dibutyl-N'-(benzoyl)thioharnstoff In ethanol for 2h; Heating;	80%

benzyl bromide (100-39-0) + L-tyrosine (60-18-4) → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
Stage #1: L-tyrosine With sodium hydroxide; copper(II) sulfate for 1h; Heating; Stage #2: benzyl bromide With sodium hydroxide In methanol at 20℃;	73%
Stage #1: L-tyrosine With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 70℃; for 1h; Stage #2: benzyl bromide With sodium hydroxide In methanol at 70℃; for 0.5h;	68%
Stage #1: L-tyrosine With copper(ll) sulfate pentahydrate; sodium hydroxide In water at 20 - 70℃; Stage #2: benzyl bromide With sodium hydroxide In methanol; water Enzymatic reaction; Stage #3: With edetate disodium In water at 70℃; for 4.5h;	68%

L-tyrosine (60-18-4) + benzyl chloride (100-44-7) → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
Stage #1: L-tyrosine With potassium hydroxide; copper(II) sulfate In water at 15 - 65℃; for 1h; Stage #2: benzyl chloride In water; N,N-dimethyl-formamide at 20 - 55℃; for 2h; Stage #3: With hydrogenchloride; ammonia more than 3 stages;	62%

O-benzyl-L-tyrosine coper complex + hydrogenchloride (7647-01-0) → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
Stage #1: O-benzyl-L-tyrosine coper complex; hydrogenchloride In water at 26 - 28℃; Stage #2: With ammonia In water Product distribution / selectivity;	46%

benzyl bromide (100-39-0) + copper (II)-salt of L-tyrosine → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
With sodium hydroxide
With sodium hydroxide

copper(I) sulfate + L-tyrosine (60-18-4) + benzyl chloride (100-44-7) → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
With copper(II) sulfate In methanol; sodium hydroxide; water

copper(I) sulfate + benzyl bromide (100-39-0) + L-tyrosine (60-18-4) → O-benzyl-S-tyrosine (16652-64-5)

Conditions	Yield
With copper(II) sulfate In methanol; sodium hydroxide; water
With copper(II) sulfate In methanol; sodium hydroxide; water
With copper(II) sulfate In methanol; sodium hydroxide; water

ethanol (64-17-5) + O-benzyl-S-tyrosine (16652-64-5) → O-benzyl L-tyrosine ethyl ester (19842-36-5)

Conditions	Yield
With thionyl chloride at 20℃; for 12h;	100%
With hydrogenchloride

O-benzyl-S-tyrosine (16652-64-5) + Heptanoic acid chloride (2528-61-2) → (S)-3-(4-Benzyloxy-phenyl)-2-heptanoylamino-propionic acid (196704-18-4)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 4h; Ambient temperature;	99%
With sodium hydroxide In tetrahydrofuran; water for 5h; Acylation;	99%

Ala-OtBu (21691-50-9) + O-benzyl-S-tyrosine (16652-64-5) → H-L-Tyr(Bn)-L-Ala-OtBu

Conditions	Yield
Stage #1: O-benzyl-S-tyrosine With 1H-imidazole; tris[(1,1,1,3,3,3-hexafluoropropan-2-yl)oxy]silane; cesium fluoride In chloroform at 30℃; for 1h; Inert atmosphere; Sealed tube; Stage #2: With N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide In chloroform at 30℃; for 1h; Inert atmosphere; Sealed tube; Stage #3: Ala-OtBu In chloroform at 30℃; for 6h; Inert atmosphere; Sealed tube;	99%

methanol (67-56-1) + O-benzyl-S-tyrosine (16652-64-5) → methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride (34805-17-9)

Conditions	Yield
With thionyl chloride for 72h; Ambient temperature;	98%
With thionyl chloride at 0℃; Reflux;	90%

O-benzyl-S-tyrosine (16652-64-5) + benzyl chloroformate (501-53-1) → N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1, 92455-53-3, 16677-29-5)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2h;	95%
With sodium hydroxide

O-benzyl-S-tyrosine (16652-64-5) + trichloromethyl chloroformate (503-38-8) → N-Carboxy-O-benzyl-L-tyrosine Anhydride (22831-96-5)

Conditions	Yield
In tetrahydrofuran at 55℃; for 2h; Temperature;	93.3%

O-benzyl-S-tyrosine (16652-64-5) → 2-[4-(benzyloxy)phenyl]acetonitrile (838-96-0)

Conditions	Yield
With sodium hydroxide; trichloroisocyanuric acid at 25℃; for 1h;	93%

pentamethylbenzene, (700-12-9) + O-benzyl-S-tyrosine (16652-64-5) → (2,3,4,5,6-pentamethylphenyl)phenylmethane (39502-94-8)

Conditions	Yield
With trifluoroacetic acid for 7h; Ambient temperature;	91%

O-benzyl-S-tyrosine (16652-64-5) + cobalt(II) chloride (7646-79-9) → [(C6H5CH2OC6H4CH2CH(NH2)COO)2Co]

Conditions	Yield
In tetrahydrofuran mixing of soln. of PhCH2OC6H4CH2CH(NH2)CO2H in THF with CoCl2 (0.5 equiv.), stirring for 3 h at 50-60°C; removal of solvent, washing several times with Et2O, MeOH and H2O, elem.anal.;	90%

O-benzyl-S-tyrosine (16652-64-5) + ethyl acetoacetate (141-97-9) + N-cyclohexyl-cyclohexanamine (101-83-7) → (Z)-3-[(S)-2-(4-Benzyloxy-phenyl)-1-carboxy-ethylamino]-but-2-enoic acid ethyl ester; compound with dicyclohexyl-amine (114671-46-4)

Conditions	Yield
In methanol; ethanol; water for 3h; Heating;	89%

O-benzyl-S-tyrosine (16652-64-5) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → O-benzyl-N-Tcc-L-tyrosine (37888-25-8)

Conditions	Yield
In ethyl acetate Heating;	85%

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (3496-11-5) + O-benzyl-S-tyrosine (16652-64-5) → N-benzoxycarbonyl-L-valyl-O-benzyl-L-tyrosine (264887-57-2)

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 20℃; Condensation;	78%

O-benzyl-S-tyrosine (16652-64-5) → (S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol (85803-44-7)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 6h;	77%
Stage #1: O-benzyl-S-tyrosine With sodium tetrahydroborate; iodine In tetrahydrofuran for 3h; Heating; Stage #2: With potassium hydroxide In tetrahydrofuran; methanol at 20℃;	66%
Yield given. Multistep reaction;

O-benzyl-S-tyrosine (16652-64-5) + sodium acetate (127-09-3) → (S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid (267228-34-2)

Conditions	Yield
With acetic acid; isopentyl nitrite at 20℃; for 72h;	77%

O-benzyl-S-tyrosine (16652-64-5) → (S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid (162919-37-1)

Conditions	Yield
Stage #1: O-benzyl-S-tyrosine With sulfuric acid; sodium nitrite In tetrahydrofuran; water at 0 - 20℃; for 3h; Stage #2: With water In tetrahydrofuran at 10 - 20℃;	76%
With sulfuric acid; sodium nitrite In water; N,N-dimethyl-formamide at 20℃; for 13h; Inert atmosphere;	62%
Stage #1: O-benzyl-S-tyrosine With potassium hydrogensulfate In 1,4-dioxane; water at 0 - 5℃; for 1h; Stage #2: With sodium nitrite In 1,4-dioxane; water at 30℃; for 4h; Product distribution / selectivity;	50%

bis(trichloromethyl) carbonate (32315-10-9) + O-benzyl-S-tyrosine (16652-64-5) → N-Carboxy-O-benzyl-L-tyrosine Anhydride (22831-96-5)

Conditions	Yield
Stage #1: O-benzyl-S-tyrosine With Pinene In ethyl acetate Inert atmosphere; Reflux; Stage #2: bis(trichloromethyl) carbonate In ethyl acetate for 2h; Inert atmosphere; Reflux;	75%
Stage #1: O-benzyl-S-tyrosine With Pinene In ethyl acetate at 90℃; for 0.25h; Stage #2: bis(trichloromethyl) carbonate at 90℃;

formaldehyd (50-00-0) + O-benzyl-S-tyrosine (16652-64-5) → (S)-3-(4-benzyloxyphenyl)-2-(dimethylamino)propanoic acid

Conditions	Yield
With sodium cyanoborohydride; acetic acid In water; acetonitrile at 22℃; for 1h; pH=Ca.7; Inert atmosphere;	75%

phosgene (75-44-5) + O-benzyl-S-tyrosine (16652-64-5) → N-Carboxy-O-benzyl-L-tyrosine Anhydride (22831-96-5)

Conditions	Yield
In tetrahydrofuran; toluene at 50℃; for 1.5h;	74.3%
In tetrahydrofuran; toluene at 50℃; for 1.5h;	74.3%
In tetrahydrofuran; toluene at 50℃; for 1h;	65%

O-benzyl-S-tyrosine (16652-64-5) → (4-(benzyloxy)phenyl)(5-(4-(benzyloxy)phenyl)thiazol-2-yl)methanone

Conditions	Yield
With sodiumsulfide nonahydrate; water; iodine; acetic acid In dimethyl sulfoxide at 100℃; for 8h;	73%

di-tert-butyl dicarbonate (24424-99-5) + O-benzyl-S-tyrosine (16652-64-5) → O-benzyl-N-tert-butoxycarbonyl-L-tyrosine (2130-96-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20 - 40℃; for 18h; pH=10.4;	70%
In water; tert-butyl alcohol pH 9.5-10.0;
With sodium hydroxide; sodium hydrogencarbonate In 1,4-dioxane at 20℃;
With sodium hydroxide In water; tert-butyl alcohol at 20℃;	2.46 g
Stage #1: O-benzyl-S-tyrosine With sodium hydroxide In water; tert-butyl alcohol Cooling with ice; Stage #2: di-tert-butyl dicarbonate In water; tert-butyl alcohol at 20℃; Stage #3: With hydrogenchloride In water; tert-butyl alcohol	2.46 g

O-benzyl-S-tyrosine (16652-64-5) → (4-(benzyloxy)phenyl)(5-(4-(benzyloxy)phenyl)oxazol-2-yl)methanone

Conditions	Yield
With water; iodine; trifluoroacetic acid In dimethyl sulfoxide at 120℃; for 8h;	66%

methanol (67-56-1) + O-benzyl-S-tyrosine (16652-64-5) → O-benzyltyrosine methyl ester (57177-83-0)

Conditions	Yield
With thionyl chloride at 40℃; for 4h; Esterification;	64%

O-benzyl-S-tyrosine (16652-64-5) + zinc diacetate (557-34-6) → [(C6H5CH2OC6H4CH2CH(NH2)COO)2Zn]

Conditions	Yield
With sodium hydroxide In methanol; water addn. of soln. of PhCH2OC6H4CH2CH(NH2)CO2H in MeOH to aq. NaOH and Zn(OAc)2 (0.5 equiv.), stirring for 3 h at 50-60°C; removal of solvent, washing several times with Et2O, MeOH and H2O, elem.anal.;	63%

di-tert-butyl dicarbonate (24424-99-5) + O-benzyl-S-tyrosine (16652-64-5) → Tyr(Bn)-tBu.HCl

Conditions	Yield
Stage #1: di-tert-butyl dicarbonate; O-benzyl-S-tyrosine With sodium hydrogencarbonate In tetrahydrofuran; water for 3h; Stage #2: With tert-Butyl 2,2,2-trichloroacetimidate In tetrahydrofuran Stage #3: With hydrogenchloride; trifluoroacetic acid In dichloromethane; water	60%

O-benzyl-S-tyrosine (16652-64-5) + bromoacetic acid methyl ester (96-32-2) → (methoxycarbonyl)methyl 2-(bis(methoxycarbonylmethyl)-L-amino)-3-(4-(benzyloxy)phenyl)propionate (1022087-04-2)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium carbonate In various solvent(s) at 108℃; for 16h;	55%

Upstream product

• 60-18-4 L-tyrosine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 7647-01-0 hydrogenchloride 
• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 

Downstream Products

• 2130-96-3 O-benzyl-N-tert-butoxycarbonyl-L-tyrosine 
• 37888-23-6 2-Chlorethoxycarbonyl-L-tyrosin-benzylether 
• 114671-46-4 (Z)-3-[(S)-2-(4-Benzyloxy-phenyl)-1-carboxy-ethylamino]-but-2-enoic acid ethyl ester; compound with dicyclohexyl-amine 
• 196704-18-4 (S)-3-(4-Benzyloxy-phenyl)-2-heptanoylamino-propionic acid 
• 374803-66-4 (S)-2-[2-Benzoyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenylamino]-3-(4-benzyloxy-phenyl)-propionic acid 
• 199340-29-9 Heptanoic acid [(S)-1-{3-[4-(3-amino-propylamino)-butylamino]-propylcarbamoyl}-2-(4-benzyloxy-phenyl)-ethyl]-amide 
• 199340-31-3 (3-tert-Butoxycarbonylamino-propyl)-[4-(tert-butoxycarbonyl-{3-[(S)-2-heptanoylamino-3-(4-hydroxy-phenyl)-propionylamino]-propyl}-amino)-butyl]-carbamic acid tert-butyl ester 
• 199340-32-4 (3-tert-Butoxycarbonylamino-propyl)-[4-(tert-butoxycarbonyl-{3-[(S)-2-heptanoylamino-3-(4-methoxy-phenyl)-propionylamino]-propyl}-amino)-butyl]-carbamic acid tert-butyl ester 
• 199340-30-2 [4-({3-[(S)-3-(4-Benzyloxy-phenyl)-2-heptanoylamino-propionylamino]-propyl}-tert-butoxycarbonyl-amino)-butyl]-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester 
• 199340-34-6 {(S)-5-Benzyloxycarbonylamino-5-[3-(4-{3-[(S)-2-heptanoylamino-3-(4-methoxy-phenyl)-propionylamino]-propylamino}-butylamino)-propylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester 
• 199340-36-8 [(S)-5-Amino-5-(3-{tert-butoxycarbonyl-[4-(tert-butoxycarbonyl-{3-[(S)-2-heptanoylamino-3-(4-methoxy-phenyl)-propionylamino]-propyl}-amino)-butyl]-amino}-propylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester 
• 199340-35-7 [(S)-5-Benzyloxycarbonylamino-5-(3-{tert-butoxycarbonyl-[4-(tert-butoxycarbonyl-{3-[(S)-2-heptanoylamino-3-(4-methoxy-phenyl)-propionylamino]-propyl}-amino)-butyl]-amino}-propylcarbamoyl)-pentyl]-carbamic acid tert-butyl ester 
• 199340-37-9 [(S)-5-(3-{tert-Butoxycarbonyl-[4-(tert-butoxycarbonyl-{3-[(S)-2-heptanoylamino-3-(4-methoxy-phenyl)-propionylamino]-propyl}-amino)-butyl]-amino}-propylcarbamoyl)-5-(2-diazo-3,3,3-trifluoro-propionylamino)-pentyl]-carbamic acid tert-butyl ester 
• 199340-33-5 Heptanoic acid [(S)-1-{3-[4-(3-amino-propylamino)-butylamino]-propylcarbamoyl}-2-(4-methoxy-phenyl)-ethyl]-amide 

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