O-benzyl-S-tyrosine
Conditions | Yield |
---|---|
With sodium sulfide In water at 25 - 30℃; for 0.166667h; | 93% |
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine
O-benzyl-S-tyrosine
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; |
O-benzyl-S-tyrosine
Conditions | Yield |
---|---|
With N,N-Dibutyl-N'-(benzoyl)thioharnstoff In ethanol for 2h; Heating; | 80% |
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% |
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% |
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
O-benzyl-S-tyrosine
Conditions | Yield |
---|---|
With sodium hydroxide | |
With sodium hydroxide |
Conditions | Yield |
---|---|
With copper(II) sulfate In methanol; sodium hydroxide; water |
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 |
Conditions | Yield |
---|---|
With thionyl chloride at 20℃; for 12h; | 100% |
With hydrogenchloride |
O-benzyl-S-tyrosine
Heptanoic acid chloride
(S)-3-(4-Benzyloxy-phenyl)-2-heptanoylamino-propionic acid
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran for 4h; Ambient temperature; | 99% |
With sodium hydroxide In tetrahydrofuran; water for 5h; Acylation; | 99% |
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
O-benzyl-S-tyrosine
methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride for 72h; Ambient temperature; | 98% |
With thionyl chloride at 0℃; Reflux; | 90% |
O-benzyl-S-tyrosine
benzyl chloroformate
N-benzyloxycarbonyl-O-benzyl-L-tyrosine
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2h; | 95% |
With sodium hydroxide |
O-benzyl-S-tyrosine
trichloromethyl chloroformate
N-Carboxy-O-benzyl-L-tyrosine Anhydride
Conditions | Yield |
---|---|
In tetrahydrofuran at 55℃; for 2h; Temperature; | 93.3% |
O-benzyl-S-tyrosine
2-[4-(benzyloxy)phenyl]acetonitrile
Conditions | Yield |
---|---|
With sodium hydroxide; trichloroisocyanuric acid at 25℃; for 1h; | 93% |
pentamethylbenzene,
O-benzyl-S-tyrosine
(2,3,4,5,6-pentamethylphenyl)phenylmethane
Conditions | Yield |
---|---|
With trifluoroacetic acid for 7h; Ambient temperature; | 91% |
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
ethyl acetoacetate
N-cyclohexyl-cyclohexanamine
(Z)-3-[(S)-2-(4-Benzyloxy-phenyl)-1-carboxy-ethylamino]-but-2-enoic acid ethyl ester; compound with dicyclohexyl-amine
Conditions | Yield |
---|---|
In methanol; ethanol; water for 3h; Heating; | 89% |
O-benzyl-S-tyrosine
2,2,2-Trichloroethyl chloroformate
O-benzyl-N-Tcc-L-tyrosine
Conditions | Yield |
---|---|
In ethyl acetate Heating; | 85% |
2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate
O-benzyl-S-tyrosine
N-benzoxycarbonyl-L-valyl-O-benzyl-L-tyrosine
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran; water at 20℃; Condensation; | 78% |
O-benzyl-S-tyrosine
(S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol
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
sodium acetate
(S)-2-acetoxy-3-(4-(benzyloxy)phenyl)propanoic acid
Conditions | Yield |
---|---|
With acetic acid; isopentyl nitrite at 20℃; for 72h; | 77% |
O-benzyl-S-tyrosine
(S)-3-(4-(benzyloxy)phenyl)-2-hydroxypropanoic acid
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
O-benzyl-S-tyrosine
N-Carboxy-O-benzyl-L-tyrosine Anhydride
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
O-benzyl-S-tyrosine
Conditions | Yield |
---|---|
With sodium cyanoborohydride; acetic acid In water; acetonitrile at 22℃; for 1h; pH=Ca.7; Inert atmosphere; | 75% |
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
Conditions | Yield |
---|---|
With sodiumsulfide nonahydrate; water; iodine; acetic acid In dimethyl sulfoxide at 100℃; for 8h; | 73% |
di-tert-butyl dicarbonate
O-benzyl-S-tyrosine
O-benzyl-N-tert-butoxycarbonyl-L-tyrosine
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
Conditions | Yield |
---|---|
With water; iodine; trifluoroacetic acid In dimethyl sulfoxide at 120℃; for 8h; | 66% |
Conditions | Yield |
---|---|
With thionyl chloride at 40℃; for 4h; Esterification; | 64% |
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% |
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
bromoacetic acid methyl ester
(methoxycarbonyl)methyl 2-(bis(methoxycarbonylmethyl)-L-amino)-3-(4-(benzyloxy)phenyl)propionate
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; potassium carbonate In various solvent(s) at 108℃; for 16h; | 55% |
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