Boc-L-Tyrosine methyl ester supplier

Name
Boc-L-Tyrosine methyl ester
EINECS 1533716-785-6
CAS No. 4326-36-7
Article Data105
CAS DataBase
Density 1.169 g/cm³
Solubility
Melting Point 100-104 °C(lit.)
Formula C₁₅H₂₁NO₅
Boiling Point 452.7 °C at 760 mmHg
Molecular Weight 295.335
Flash Point 227.6 °C
Transport Information
Appearance
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms methyl (2S)-3-(4-hydroxyphenyl)-2-(tert-butoxycarbonylamino)propanoate;Boc-Tyr-OMe;N-BOC-L-Tyr-Ome;N-Boc-L-Tyrosine Methyl ester;
PSA 84.86000
LogP 2.39190

Synthetic route

: 24424-99-5
di-tert-butyl dicarbonate

: 1080-06-4
L-Tyr-OMe

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 20℃; for 15h;	100%
With triethylamine In dichloromethane	100%
In tetrahydrofuran at 20℃; for 14.1667h;	97%

: 24424-99-5
di-tert-butyl dicarbonate

: 3417-91-2
L-tyrosine methyl ester HCl

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With TEA In N,N-dimethyl-formamide at 60℃; for 0.5h;	100%
With triethylamine In methanol at 0 - 20℃; for 2.25h;	100%
Stage #1: L-tyrosine methyl ester HCl With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃;	99%

: 3978-80-1
Boc-Tyr-OH

: 74-88-4
methyl iodide

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.566667h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	88%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 20h;	85%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	65%
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 5h;

: 3978-80-1
Boc-Tyr-OH

: 77-78-1
dimethyl sulfate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran for 2h; Methylation; esterification; Heating;	100%

: 67-56-1
methanol

: 24424-99-5
di-tert-butyl dicarbonate

: 60-18-4
L-tyrosine

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: methanol; L-tyrosine With thionyl chloride for 3h; Inert atmosphere; Heating; Stage #2: di-tert-butyl dicarbonate With triethylamine In methanol for 20h; Inert atmosphere;	100%
Stage #1: methanol; L-tyrosine With thionyl chloride Heating; Stage #2: di-tert-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; Further stages.;

...Expand

: 147363-23-3
methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]-propanoate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With dimethylamine borane; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; deallylation;	90%
With tetrakis(triphenylphosphine) palladium(0); phenylsilane In dichloromethane Ambient temperature;	77%
With cisplatin In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 24h; pH=7.4;

: 1671-87-0
3,6-di(2'-pyridyl)-1,2,4,5-tetrazine

: O-vinyl-N-(tert-butoxycarbonyl)-L-tyrosine methyl ester

A: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

B: 36901-11-8
3,6-di(pyridin-2'-yl)-s-tetrazine

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 72h; Inert atmosphere;	A 68% B 65%

...Expand

: 113850-76-3
N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With oxygen; triethylamine In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation;	58%

: 106-41-2
4-bromo-phenol

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: 4-bromo-phenol With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 50℃; for 3h; Negishi coupling; Inert atmosphere;	51%
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 4-bromo-phenol With tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 50℃; for 2h; Negishi cross-coupling; Further stages.;	23%

: 540-38-5
4-Iodophenol

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

A: 915040-50-5
(2S,5S)-2,5-bis-tert-butoxycarbonylaminohexane-1,6-dioic acid dimethyl ester

B: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); zinc In water at 65℃; for 4h; Negishi coupling reaction; Inert atmosphere;	A n/a B 35%

...Expand

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 1080-06-4
L-Tyr-OMe

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With pyridine

: 27513-44-6
N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 2h; Hydrogenolysis;
With pyridine; hydrogen; palladium on activated charcoal In methanol at 20℃; Product distribution; Further Variations:; Reagents; time, other benzyl ethers;

: 19578-68-8
4-(4-benzyloxyphenyl) iodide

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

A: 28875-17-4
(S)-N-(tert-butoxycarbonyl)alanine methyl ester

B: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: 4-(4-benzyloxyphenyl) iodide; N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With dichlorobis(tri-O-tolylphosphine)palladium; zinc In tetrahydrofuran; N,N-dimethyl acetamide at 60℃; for 3h; Condensation; Stage #2: With hydrogen; palladium on activated charcoal In tetrahydrofuran at 20℃; for 21h; Hydrogenolysis;	A n/a B 1.80 g

...Expand

: (S)-methyl 3-(4-acetoxyphenyl)-2-(tert-butoxycarbonylamino)propanoate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
natural kaolinitic clay In methanol at 25℃; for 0.5h;

: 60-18-4
L-tyrosine

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / SOCl2 2: 85 percent / Et3N View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 20 h / Heating 2: triethylamine / methanol / 17 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 0 - 20 °C / Inert atmosphere 2: sodium hydrogencarbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / hexane / 8 h / 20 °C 2: 76 percent / 1,2-dimethoxy-ethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 92 percent / benzene / 6 h / 20 °C 2: 76 percent / 1,2-dimethoxy-ethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 9.8 g / Et3N / H2O; dioxane / 0 deg C, 30 min; 25 deg C, 24 h 2: 85 percent / NaHCO3 / dimethylformamide / 20 h / 25 °C View Scheme

: 946-80-5
(benzyloxy)benzene

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 96 percent / HgO; I2 / CH2Cl2 / 26 h / 20 °C 2.1: Zn; PdCl2[P(o-tol)3]2 / tetrahydrofuran; N,N-dimethyl-acetamide / 3 h / 60 °C 2.2: 1.80 g / H2 / Pd/C / tetrahydrofuran / 21 h / 20 °C View Scheme

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

poly<4-(1-hydroxybenzotriazol-6-yl)methylstyrene: poly<4-(1-hydroxybenzotriazol-6-yl)methylstyrene

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / dimethylformamide / 15 h / 20 °C 2: H2 / Pd/C / methanol / 2 h / 20 °C View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: 1080-06-4
L-Tyr-OMe

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With sodium hydrogencarbonate In ethanol at 20℃; for 15h;	100%
With triethylamine In dichloromethane	100%
In tetrahydrofuran at 20℃; for 14.1667h;	97%

: 24424-99-5
di-tert-butyl dicarbonate

: 3417-91-2
L-tyrosine methyl ester HCl

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With TEA In N,N-dimethyl-formamide at 60℃; for 0.5h;	100%
With triethylamine In methanol at 0 - 20℃; for 2.25h;	100%
Stage #1: L-tyrosine methyl ester HCl With triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃;	99%

: 3978-80-1
Boc-Tyr-OH

: 74-88-4
methyl iodide

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.566667h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	88%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25℃; for 20h;	85%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	65%
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 5h;

: 3978-80-1
Boc-Tyr-OH

: 77-78-1
dimethyl sulfate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran for 2h; Methylation; esterification; Heating;	100%

: 67-56-1
methanol

: 24424-99-5
di-tert-butyl dicarbonate

: 60-18-4
L-tyrosine

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: methanol; L-tyrosine With thionyl chloride for 3h; Inert atmosphere; Heating; Stage #2: di-tert-butyl dicarbonate With triethylamine In methanol for 20h; Inert atmosphere;	100%
Stage #1: methanol; L-tyrosine With thionyl chloride Heating; Stage #2: di-tert-butyl dicarbonate With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; Further stages.;

...Expand

: 147363-23-3
methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]-propanoate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With dimethylamine borane; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; deallylation;	90%
With tetrakis(triphenylphosphine) palladium(0); phenylsilane In dichloromethane Ambient temperature;	77%
With cisplatin In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 24h; pH=7.4;

: 67-56-1
methanol

: 24424-99-5
di-tert-butyl dicarbonate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: methanol; L-tyrosine With thionyl chloride at 0℃; for 3h; Heating / reflux; Stage #2: di-tert-butyl dicarbonate With triethylamine In acetonitrile at 20℃; for 1.5h; Stage #3: With sodium hydrogen sulfate; sodium carbonate more than 3 stages;	90%
Stage #1: methanol; L-tyrosine With thionyl chloride for 3h; Heating / reflux; Stage #2: di-tert-butyl dicarbonate With triethylamine In acetonitrile at 20℃; for 1.5h;	90%

: (S)-methyl 2-(((tert-butoxy)carbonyl)amino)-3-{4-[(2-methoxyacetyl)oxy]phenyl}propanoate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;	86%

: 67-56-1
methanol

: 3978-80-1
Boc-Tyr-OH

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 7h; Inert atmosphere;	85%
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane for 21h;	78%
With acetyl chloride for 0.75h; Reflux;	71%
With ammonium cerium(IV) nitrate at 25℃;	62%
With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 7h;	56%

: 112766-18-4
methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; carbon monoxide; palladium diacetate; potassium carbonate In N,N-dimethyl-formamide at 70℃; for 5h; Reagent/catalyst;	84.7%

: 24424-99-5
di-tert-butyl dicarbonate

: L-tyrosine methyl ester hydrochloride

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: L-tyrosine methyl ester hydrochloride With potassium hydrogencarbonate In water at 20℃; for 1.5h; Stage #2: di-tert-butyl dicarbonate In water; acetone at 20℃; for 0.5h;	84%

: 540-38-5
4-Iodophenol

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: p-Iodophenol With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 20℃; Negishi coupling; Inert atmosphere;	82%
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With chloro-trimethyl-silane; zinc In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: p-Iodophenol With tris-(o-tolyl)phosphine; tris(dibenzylideneacetone)dipalladium (0) In N,N-dimethyl-formamide at 20℃; Further stages.;	106 mg

: 1187581-89-0
C20H29NO7

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With bismuth(III) bromide; water In acetonitrile at 65℃; for 12h;	82%

: tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

: 3417-91-2
L-tyrosine methyl ester HCl

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 38 - 40℃;	82%

: 3417-91-2
L-tyrosine methyl ester HCl

: 404586-94-3
1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline

A: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

B: (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butoxycarbonyl)oxy)-2-methoxyphenyl)propanoate

Conditions

Conditions	Yield
In 1,2-dimethoxyethane at 20℃;	A 76% B n/a

...Expand

: 1671-87-0
3,6-di(2'-pyridyl)-1,2,4,5-tetrazine

: O-vinyl-N-(tert-butoxycarbonyl)-L-tyrosine methyl ester

A: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

B: 36901-11-8
3,6-di(pyridin-2'-yl)-s-tetrazine

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 72h; Inert atmosphere;	A 68% B 65%

...Expand

: 113850-76-3
N-(tert-butoxycarbonyl)-4-iodo-L-phenylalanine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With oxygen; triethylamine In acetonitrile at 32℃; for 24h; Schlenk technique; UV-irradiation;	58%

: 106-41-2
4-bromo-phenol

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: 4-bromo-phenol With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0) In N,N-dimethyl-formamide at 50℃; for 3h; Negishi coupling; Inert atmosphere;	51%
Stage #1: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With iodine; zinc In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 4-bromo-phenol With tris-(o-tolyl)phosphine; palladium diacetate In N,N-dimethyl-formamide at 50℃; for 2h; Negishi cross-coupling; Further stages.;	23%

: 540-38-5
4-Iodophenol

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

A: 915040-50-5
(2S,5S)-2,5-bis-tert-butoxycarbonylaminohexane-1,6-dioic acid dimethyl ester

B: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With N,N,N,N,-tetramethylethylenediamine; dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); zinc In water at 65℃; for 4h; Negishi coupling reaction; Inert atmosphere;	A n/a B 35%

...Expand

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 1080-06-4
L-Tyr-OMe

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With pyridine

: 27513-44-6
N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 2h; Hydrogenolysis;
With pyridine; hydrogen; palladium on activated charcoal In methanol at 20℃; Product distribution; Further Variations:; Reagents; time, other benzyl ethers;

: 19578-68-8
4-(4-benzyloxyphenyl) iodide

: 93267-04-0
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

A: 28875-17-4
(S)-N-(tert-butoxycarbonyl)alanine methyl ester

B: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Stage #1: 4-(4-benzyloxyphenyl) iodide; N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester With dichlorobis(tri-O-tolylphosphine)palladium; zinc In tetrahydrofuran; N,N-dimethyl acetamide at 60℃; for 3h; Condensation; Stage #2: With hydrogen; palladium on activated charcoal In tetrahydrofuran at 20℃; for 21h; Hydrogenolysis;	A n/a B 1.80 g

...Expand

: (S)-methyl 3-(4-acetoxyphenyl)-2-(tert-butoxycarbonylamino)propanoate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
natural kaolinitic clay In methanol at 25℃; for 0.5h;

: 60-18-4
L-tyrosine

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / SOCl2 2: 85 percent / Et3N View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 20 h / Heating 2: triethylamine / methanol / 17 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: thionyl chloride / 0 - 20 °C / Inert atmosphere 2: sodium hydrogencarbonate / tetrahydrofuran; methanol / 20 °C / Inert atmosphere View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / hexane / 8 h / 20 °C 2: 76 percent / 1,2-dimethoxy-ethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 92 percent / benzene / 6 h / 20 °C 2: 76 percent / 1,2-dimethoxy-ethane / 20 °C View Scheme
Multi-step reaction with 2 steps 1: 9.8 g / Et3N / H2O; dioxane / 0 deg C, 30 min; 25 deg C, 24 h 2: 85 percent / NaHCO3 / dimethylformamide / 20 h / 25 °C View Scheme

: 946-80-5
(benzyloxy)benzene

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 96 percent / HgO; I2 / CH2Cl2 / 26 h / 20 °C 2.1: Zn; PdCl2[P(o-tol)3]2 / tetrahydrofuran; N,N-dimethyl-acetamide / 3 h / 60 °C 2.2: 1.80 g / H2 / Pd/C / tetrahydrofuran / 21 h / 20 °C View Scheme

: 2130-96-3
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine

poly<4-(1-hydroxybenzotriazol-6-yl)methylstyrene: poly<4-(1-hydroxybenzotriazol-6-yl)methylstyrene

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / dimethylformamide / 15 h / 20 °C 2: H2 / Pd/C / methanol / 2 h / 20 °C View Scheme

: 60-18-4
L-tyrosine

2-halogen-ethanol-(1): 2-halogen-ethanol-(1)

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. HCl / 24 h / Ambient temperature 2: 93 percent / NaHCO3 / CH2Cl2 / 2 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 9.8 g / Et3N / H2O; dioxane / 0 deg C, 30 min; 25 deg C, 24 h 2: 85 percent / NaHCO3 / dimethylformamide / 20 h / 25 °C View Scheme

: 60-18-4
L-tyrosine

KOH-solution: KOH-solution

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / 3A sieves, HCl (gas) / 2.5 h / Heating 2: 100 percent / TEA / dimethylformamide / 0.5 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: 95 percent / HCl (gas) / 2 h / 25 °C 2: 72 percent / tetrahydrofuran / 2 h / 25 °C View Scheme

: 3417-91-2
L-tyrosine methyl ester HCl

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 358-23-6
trifluoromethylsulfonic anhydride

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 112766-18-4
methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 5℃; for 2.5h;	100%
With 2,6-dimethylpyridine In dichloromethane at 0℃;	99%
With 4-methyl-morpholine In dichloromethane at -15 - -5℃; for 2.16667h;	98%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 100-39-0
benzyl bromide

: 27513-44-6
N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetone for 4h; Heating;	100%
With potassium carbonate In acetone for 24h; Heating;	99%
With potassium carbonate; potassium iodide In acetone Reflux;	99%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 640721-03-5
[[6-bromo-7-(methoxymethoxy)coumarin-4-yl]methoxy]carbonyl chloride

: 640721-07-9
O-[[[6-bromo-7-(methoxymethoxy)coumarin-4-yl]methoxy]carbonyl]-N-tert-butoxycarbonyl-L-tyrosine methyl ester

Conditions

Conditions	Yield
With dmap In acetonitrile at 20℃; for 0.25h;	100%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 89031-84-5
3-(tert-butyldimethylsilyloxy)propyl bromide

: 850655-19-5
(S)-methyl 2-(tert-butoxycarbonylamino)-3-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-phenyl)propanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 80℃; for 19h;	100%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 598-31-2
1-bromoacetone

: 170124-00-2
N-(tert-Butyloxycarbonyl)-O-(2-oxopropyl)-L-tyrosine methyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetone Reflux;	100%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 3355-28-0
1-Bromo-2-butyne

: methyl (S)-2-tert-butoxycarbonylamino-3-(4-but-2-ynyloxy-phenyl)-propionate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h; Inert atmosphere;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	30%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 19h;

: 64992-03-6
4-(bromomethyl)-2-fluoropyridine

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: methyl (S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(2-fluoropyridin-4-yl)methoxy]phenyl}propanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 17h; Williamson Ether Synthesis; Inert atmosphere;	100%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 766-80-3
1-bromomethyl-3-chlorobenzene

: (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-((3-chlorobenzyl)oxy)phenyl)propanoate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 19h; Reflux;	100%

: 74-96-4
ethyl bromide

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 92507-32-9
O-ethyl-N-tert-butoxycarbonyl-L-tyrosine methyl ester

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 30℃; for 5h; Large scale;	99.7%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 112196-57-3
methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-((tert-butyldimethylsilyl)-oxy)phenyl)propanoate

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 6h;	99%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;	99%
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 6h;	93%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 106-95-6
allyl bromide

: 147363-23-3
methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-[4-(prop-2-en-1-yloxy)phenyl]-propanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h;	99%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;	98%
With tetra-(n-butyl)ammonium iodide; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;	95%

: 4326-36-7
(S)-N-(tert-butoxycarbonyl)tyrosine methyl ester

: 83345-46-4
N-(tert-butyloxycarbonyl)-L-tyrosinol

Conditions

Conditions	Yield
With sodium tetrahydroborate; calcium chloride	99%
With sodium tetrahydroborate In methanol	93%
With sodium tetrahydroborate; lithium chloride In tetrahydrofuran for 72h; Heating;	73%
With lithium aluminium tetrahydride In tetrahydrofuran at 5 - 10℃; for 96h;	70%
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 12h; Reflux; Inert atmosphere;	69.6%

Boc-L-Tyrosine methyl ester Chemical Properties

Molecule structure of Boc-L-Tyrosine methyl ester (CAS NO.4326-36-7):

IUPAC Name: Methyl (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
Molecular Weight: 295.33094 g/mol
Molecular Formula: C₁₅H₂₁NO₅
Density: 1.169 g/cm³
Melting Point: 100-104 °C(lit.)
Boiling Point: 452.7 °C at 760 mmHg
Flash Point: 227.6 °C
Index of Refraction: 1.523
Molar Refractivity: 77.18 cm³
Molar Volume: 252.4 cm³
Surface Tension: 43.2 dyne/cm
Enthalpy of Vaporization: 73.93 kJ/mol
Vapour Pressure: 8.19E-09 mmHg at 25 °C
XLogP3: 1.7
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 7
Tautomer Count: 4
Exact Mass: 295.141973
MonoIsotopic Mass: 295.141973
Topological Polar Surface Area: 84.9
Heavy Atom Count: 21
Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)O)C(=O)OC
Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)OC
InChI: InChI=1S/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(18)20-4)9-10-5-7-11(17)8-6-10/h5-8,12,17H,9H2,1-H3,
(H,16,19)/t12-/m0/s1
InChIKey: NQIFXJSLCUJHBB-LBPRGKRZSA-N
Product Categories of Boc-L-Tyrosine methyl ester (CAS NO.4326-36-7): Amino Acids; Tyrosine [Tyr, Y]; Boc-Amino Acids and Derivative; Amino Acids (N-Protected); Biochemistry; Boc-Amino Acids; Boc-Amino acid series

Boc-L-Tyrosine methyl ester Safety Profile

WGK Germany: 3

Boc-L-Tyrosine methyl ester Specification

Boc-L-Tyrosine methyl ester (CAS NO.4326-36-7) is also named as L-tyrosine, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester ; Methyl N-(tert-butoxycarbonyl)-L-tyrosinate ; N-(tert-Butoxycarbonyl)-L-tyrosine methyl ester .

Product Name

Boc-L-Tyrosine methyl ester

Synthetic route

Boc-L-Tyrosine methyl ester Chemical Properties

Boc-L-Tyrosine methyl ester Safety Profile

Boc-L-Tyrosine methyl ester Specification

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