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(R)-3-Naphthalen-1-yl-2-((4S,5R)-2-oxo-4,5-diphenyl-oxazolidin-3-yl)-propionic acid benzyl ester
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
With hydrogen; palladium dihydroxide In tetrahydrofuran; methanol under 3102.9 Torr; for 19h; | 89% |
(R)-2-Acetylamino-3-naphthalen-1-yl-propionic acid ethyl ester
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 55% |
A
L-1-naphthylalanine
B
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
With hydrogenchloride Heating; |
diethyl (N-acetylamino)[(1-naphthyl)methyl]malonate
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 87 percent / 1 M NaOH / aq. ethanol / 6 h / Ambient temperature 2: 94 percent / 0.17 h / 160 °C 3: 96 percent 4: 55 percent / 6 N aq. HCl / 2 h / Heating View Scheme |
2-Acetylamino-2-naphthalen-1-ylmethyl-malonic acid monoethyl ester
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 94 percent / 0.17 h / 160 °C 2: 96 percent 3: 55 percent / 6 N aq. HCl / 2 h / Heating View Scheme |
2-Acetylamino-3-naphthalen-1-yl-propionic acid ethyl ester
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent 2: 55 percent / 6 N aq. HCl / 2 h / Heating View Scheme |
2-(bromomethyl)naphthalene
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 90 percent / EtONa / ethanol / 6 h / Heating 2: 87 percent / 1 M NaOH / aq. ethanol / 6 h / Ambient temperature 3: 94 percent / 0.17 h / 160 °C 4: 96 percent 5: 55 percent / 6 N aq. HCl / 2 h / Heating View Scheme |
2-amino-3-(1-naphthyl)propanoic acid
A
L-1-naphthylalanine
B
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
With chiral stationary phase including isopropyl-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 0℃; Purification / work up; |
2-amino-3-(1-naphthyl)propanoic acid
A
3-(naphthalene-1-yl)-2-oxopropanoic acid
B
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
With L-amino acid deaminase from Proteus myxofaciens; oxygen In aq. phosphate buffer pH=7; Kinetics; Enzymatic reaction; | |
With L-amino acid deaminase from Proteus myxofaciens F318A/V412A/V438P mutant In aq. phosphate buffer at 25℃; for 2h; pH=7.5; Kinetics; Reagent/catalyst; Concentration; Resolution of racemate; Enzymatic reaction; |
3-(1-naphthyl)-D-alanine
(1S,3E)-5-<(2,5-dioxo-1-pyrrolidinyl)oxy>-1-<(1R,2E)-1-methyl-3-phenyl-2-propenyl>-5-oxo-3-pentenyl-(2S)-<3-<<(1,1-dimethylethoxy)carbonyl>amino>-2,2-dimethyl-1-oxopropoxy>-4-methylpentanoate
N-<(1,1-dimethylethoxy)carbonyl>-2,2-dimethyl-β-alanyl-(2S)-2-hydroxy-4-(methylpentanoyl)-(2E,5S,6R,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoyl-3-(1-naphthalenyl)-D-alanine
Conditions | Yield |
---|---|
With N,O-bis-(trimethylsilyl)-acetamide In N,N-dimethyl-formamide at 55 - 60℃; | 77% |
2-(4-(triphenylmethylthio)phenyl)acetic acid
D-norleucine
Boc-(R)-Ala
N-Boc-O-benzyl-L-threonine
L-4-fluorophenylalanine
Boc-Arg(MTS)-OH
Boc-Trp-OH
3-(1-naphthyl)-D-alanine
Nα-t-butoxycarbonyl-Nδ-xanthydryl-L-glutamine
Conditions | Yield |
---|---|
Stage #1: 2-(4-(triphenylmethylthio)phenyl)acetic acid With phosphorus tribromide; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide for 18h; Stage #2: With triethylsilane; trifluoroacetic acid In dichloromethane; water; N,N-dimethyl-formamide Stage #3: D-norleucine; Boc-(R)-Ala; N-Boc-O-benzyl-L-threonine; L-4-fluorophenylalanine; Boc-Arg(MTS)-OH; Boc-Trp-OH; 3-(1-naphthyl)-D-alanine; Nα-t-butoxycarbonyl-Nδ-xanthydryl-L-glutamine Further stages; | 16% |
3-(1-naphthyl)-D-alanine
CR 2194
Conditions | Yield |
---|---|
With chloroformic acid ethyl ester; triethylamine 1.) THF, -10 deg C, 15 min, 2.) THF, DMF, H2O, a) -10 deg C, 1 h, b) RT, overnight; Multistep reaction; |
methanol
3-(1-naphthyl)-D-alanine
D-3-(1-naphthyl)alanine methylester
Conditions | Yield |
---|---|
With hydrogenchloride at 0 - 20℃; for 18h; Fischer esterification; | |
Stage #1: methanol; 3-(1-naphthyl)-D-alanine With chloro-trimethyl-silane at 20℃; Stage #2: With triethylamine In methanol; diethyl ether at -10℃; for 1h; |
3-(1-naphthyl)-D-alanine
3-(naphthalene-1-yl)-2-oxopropanoic acid
Conditions | Yield |
---|---|
With oxygen; D-amino acid oxidase (M213G mutant, Rhodotorula gracilis) In phosphate buffer at 25℃; pH=8.5; Enzyme kinetics; Enzymatic reaction; | |
With oxygen; D-amino acid oxidase (wild type, yeast Rhodotorula gracilis) In phosphate buffer at 25℃; pH=8.5; Enzyme kinetics; Enzymatic reaction; |
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: HCl (gas) / 18 h / 0 - 20 °C 2: EDC; HOBT; DIPEA / dimethylformamide / 2 h / 20 °C 3: aq. LiOH / tetrahydrofuran / 1 h / 20 °C View Scheme |
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: HCl (gas) / 18 h / 0 - 20 °C 2: EDC; HOBT; DIPEA / dimethylformamide / 2 h / 20 °C View Scheme |
3-(1-naphthyl)-D-alanine
D-3-(1-naphthyl)alanine methylester
Conditions | Yield |
---|---|
With thionyl chloride In methanol at 20℃; for 21h; |
3-(1-naphthyl)-D-alanine
(S)-1-naphthylalanine methyl ester
Conditions | Yield |
---|---|
With thionyl chloride In methanol |
methanol
3-(1-naphthyl)-D-alanine
(D)-1-naphthylalanine methyl ester hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride Reflux; |
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane / 20 °C 1.2: 1 h / -10 °C 2.1: sodium tetrahydroborate / methanol / 20 °C 3.1: sodium hydroxide / 1,4-dioxane View Scheme |
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane / 20 °C 1.2: 1 h / -10 °C 2.1: sodium tetrahydroborate / methanol / 20 °C 3.1: sodium hydroxide / 1,4-dioxane 4.1: sodium hydroxide / N,N-dimethyl-formamide / 50 °C View Scheme |
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: chloro-trimethyl-silane / 20 °C 1.2: 1 h / -10 °C 2.1: sodium tetrahydroborate / methanol / 20 °C 3.1: sodium hydroxide / 1,4-dioxane 4.1: sodium hydroxide / N,N-dimethyl-formamide / 50 °C 5.1: benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 20 °C View Scheme |
3-(1-naphthyl)-D-alanine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane / 20 °C 1.2: 1 h / -10 °C 2.1: sodium tetrahydroborate / methanol / 20 °C View Scheme |
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