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Chemical Structure| 71239-85-5 Chemical Structure| 71239-85-5
Chemical Structure| 71239-85-5

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Boc-2-Pal-OH is a protected phenylalanine derivative with the amino group protected by tert-butoxycarbonyl (Boc) and a substitution on the phenyl ring, suitable for peptide synthesis.

Synonyms: N-Boc-3-(2-pyridyl)-L-alanine

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Product Details of Boc-2-Pal-OH

CAS No. :71239-85-5
Formula : C13H18N2O4
M.W : 266.29
SMILES Code : O=C(O)[C@@H](NC(OC(C)(C)C)=O)CC1=NC=CC=C1
Synonyms :
N-Boc-3-(2-pyridyl)-L-alanine
MDL No. :MFCD00191190
InChI Key :KMODKKCXWFNEIK-JTQLQIEISA-N
Pubchem ID :2734482

Safety of Boc-2-Pal-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Boc-2-Pal-OH

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 71239-85-5 ]

[ 71239-85-5 ] Synthesis Path-Downstream   1~30

  • 1
  • [ 24424-99-5 ]
  • [ 37535-51-6 ]
  • [ 71239-85-5 ]
  • 2
  • [ 71239-85-5 ]
  • 4-(2-fluoroethyl)piperidine hydrochloride [ No CAS ]
  • [ 200268-01-5 ]
  • 3
  • [ 98946-18-0 ]
  • [ 71239-85-5 ]
  • 2-<i>tert</i>-butoxycarbonylamino-3-pyridin-2-yl-propionic acid <i>tert</i>-butyl ester [ No CAS ]
  • 4
  • [ 71239-85-5 ]
  • [ 221078-04-2 ]
  • [ 553668-09-0 ]
  • 5
  • [ 71239-85-5 ]
  • [ 200268-04-8 ]
  • 6
  • [ 71239-85-5 ]
  • (S)-2-Amino-1-[4-(2-fluoro-ethyl)-piperidin-1-yl]-3-pyridin-2-yl-propan-1-one; hydrochloride [ No CAS ]
  • 7
  • [ 71239-85-5 ]
  • 4-((S)-1-Hydroxymethyl-2-phenyl-ethylamino)-pyridine-3-sulfonic acid {(S)-2-[4-(2-fluoro-ethyl)-piperidin-1-yl]-2-oxo-1-pyridin-2-ylmethyl-ethyl}-amide [ No CAS ]
  • 9
  • [ 74164-26-4 ]
  • [ 71239-85-5 ]
  • 11
  • [ 1738-76-7 ]
  • [ 71239-85-5 ]
  • [ 337530-28-6 ]
YieldReaction ConditionsOperation in experiment
With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 4 - 20℃; for 3.0h; To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(2-pyridyl)propanoic acid (55.0 g), glycine benzyl ester tosylate (69.7 g), and diphenylphosphoryl azide (46.7 ml) in N,N-dimethylformamide (550 ml) was added dropwise N,N-diisopropylethylamine (75.6 ml) at 4 C. The mixture was warmed to room temperature and stirred for 3 hours. The resulting mixture was poured into ice-cold saturated aqueous sodium hydrogencarbonate solution (700 ml). The mixture was extracted twice with ethyl acetate (total 1.3 L) and washed successively with water (400 ml×2), saturated aqueous ammonium chloride solution (200 ml), aqueous sodium hydrogencarbonate solution (300 ml×2), and brine (40 ml). The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the title compound (77.4 g) as pale brown crystals. [00175] ESI-MS: 414.3(H+H) [00176] 1H-NMR (300 MHz, CDCl3) delta 8.48 (dd, J=5 Hz,2 Hz, 1H), 7.82 (br, 1H), 7.60 (td, J=8 Hz,2 Hz, 1H), 7.40-7.29 (m, 5H), 7.21 (d, J=8 Hz, 1H), 7.14 (dd, J=8 Hz,5 Hz, 1H), 6.33 (br, 1H), 5.15 (s, 2H), 4.62 (br, 1H), 4.04 (d, J=6 Hz, 2H), 3.36-3.18 (m, 2H), 1.43 (s, 9H).
  • 12
  • 2-amino-1-[4-(4-chlorophenyl)-1-piperazinyl]ethan-1-one dihydrochloride [ No CAS ]
  • [ 71239-85-5 ]
  • [ 337530-24-2 ]
YieldReaction ConditionsOperation in experiment
Diphenylphosphoryl azide (25 g) was added to a solution of (2S)-2-(tert-butoxycarbonylamino)-3-(2-pyridyl)propanoic acid (23 g) in N,N-dimethylformamide (230 ml) at 5 C. To the mixture was added a solid of 2-amino-1-[4-(4-chlorophenyl)-1-piperazinyl]-ethan-1-one dihydrochloride (28.2 g) at 5 C. with stirring and then diisopropylethylamine (47 ml) was added dropwise at 7-10 C. The mixture was stirred at 7-10 C. for 30 minutes and at room temperature for 2 hours. The mixture was diluted with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The aqueous layer was extracted with two 500-ml portions of ethyl acetate, and the combined organic layers were extracted with 1N hydrochloric acid (150 ml×2). The combined aqueous layers were basified (pH 9) with sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed thoroughly with aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo to give the title compound (42 g). [00159] 1H-NMR (300 MHz, CDCl3) delta 1.44 (s, 9H), 3.11 (m, 4H), 3.23 (m, 1H), 3.34 (m, 1H), 3.53 (m, 2H), 3.75 (m, 2H), 4.04 (d, J=5 Hz, 2H), 4.64 (m, 1H), 6.38 (m, 1H), 6.83 (d, J=8 Hz, 2H), 7.10-7.27 (m, 4H), 7.59 (m, 1H), 7.77 (br, 1H), 8.52 (d, J=5 Hz, 1H).
  • 13
  • [ 95-83-0 ]
  • [ 71239-85-5 ]
  • [ 713138-62-6 ]
  • [ 713138-61-5 ]
  • 14
  • [ 71239-85-5 ]
  • [ 348619-79-4 ]
  • [ 37535-51-6 ]
YieldReaction ConditionsOperation in experiment
REFERENCE EXAMPLE 4 2-Amino-3-(2-pyridyl)-1-propanol (Compound A5) The title compound was obtained in a manner similar to that in Reference Examples 1 to 3 by using N-(tert-butoxycarbonyl)-beta-(2-pyridyl)-alpha-alanine as a starting material, which was derived from beta-(2-pyridyl)-alpha-alanine obtained by the method described in Bulletin Chemical Society Japan (Bull. Chem. Soc. Japan), 41, p.1634, 1968. 1H-NMR (270 MHz, CDCl3) delta 2.79 (dd, 1H, J=13.5, 7.6 Hz), 2.97 (dd, 1H, J=13.5, 5.6 Hz), 3.26 (m, 1H), 3.45 (m, 1H), 3.57 (dd, 1H, J=11.2, 4.3 Hz), 7.17-7.25 (m, 2H), 7.68 (dt, 1H, J=7.6, 2.0 Hz), 8.50 (d, 1H, J=5.0 Hz). FAB-MS: m/z 153 (M++1).
  • 15
  • [ 2462-32-0 ]
  • [ 71239-85-5 ]
  • [ 935887-93-7 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20℃; for 3.16667h; To a 0 C. solution of N-<strong>[71239-85-5]Boc-L-2-pyridylalanine</strong> (050) (1.0 g, 3.76 mmol), L-phenylalanine benzyl ester hydrochloride (002) (1.3 g, 3.76 mmol), HOBT (0.68 g, 5.0 mmol) and HBTU (1.8 g, 5.0 mmol) in tetrahydrofuran (100 mL) was added a solution of N,N-diisopropylethylamine (1.6 mL) in tetrahydrofuran (10 mL). The mixture was stirred at room temperature for another 3 hours and then diluted with ethyl acetate (200 mL), washed with saturated aqueous sodium bicarbonate (2×50 mL) and brine (100 mL) and the organic layers were dried over sodium sulfate and filtered through Celite-545. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (hexane and ethyl acetate) to provide (051) (1.45 g) which was characterized by LC/MS (LCRS (MH) m/z: 504.24).
  • 16
  • [ 71239-85-5 ]
  • [ 926018-55-5 ]
YieldReaction ConditionsOperation in experiment
99% With lithium aluminium tetrahydride; In tetrahydrofuran; for 2.0h; D. N-[(1S)-2-Hydroxy-1-(2-pyridylmethyl)ethyl](tert-butoxy)carboxamide. N-<strong>[71239-85-5]Boc-L-2-pyridylalanine</strong> (1 g, 3.7 mmol) was dissolved in THF (10 mL). Lithium aluminum hydride was added to the THF solution in small portions and then allowed to stirred for 2 hours. The reaction was quenched with saturated aqueous Na2SO4 (2 mL), and then triturated in 2-propanol. The 2-propanol mixture was filtered and then concentrated to give a colorless oil, (0.97 g, 99% yield). MS (ESI) m/z 253.1 [M+1]+.
87% A solution of 500 mg (1.88 mmol) BOC-L-2-pyridylalanine in 20 ml THF was added dropwise at 0 C. to 4 ml (4 mmol) of a 1 M solution of LiAlH4 in THF. The mixture was allowed to warm up to ambient temperature and hydrolysed after 1 h by the addition of 0.15 ml of water, 0.19 ml NaOH solution and another 0.66 ml of water. The precipitate formed was washed with water. The filtrate is freed from THF in vacuo, the residue is extracted with dichloromethane and evaporated down in vacuo.Yield: 410 mg (87%) 5.2-a
53% With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2.0h; To a solution of Boc-L-2-Pyridylalanine (1 g, 3.7 mmol) in THF (10 mL) was added dropwise 1 M solution of L1AIH4 in THF (3.7 mL) at 0 C. The reaction mixture was stirred at ambient temperature for 2 h. It was cooled in an ice-bath, and quenched with saturated aqueous Na2S04 solution (2 mL). After stirring for 1 h, the mixture was filtered through Celite, and washed with 2-propanol. The filtrate was concentrated, and the crude product was purified by column chromatography using EtOAc, then a 50:1 to 10:1 CH2CI2 / MeOH gradient to provide the title compound as a white solid (0.5 g, 53%). LC/MS m/z: 197.24 (M - ferf-butyl+H)+, 253.26 (M+H)+.
  • 17
  • [ 71239-85-5 ]
  • (4aS,8aR)-2-{1-[(2S)-2-amino-3-(pyridin-2-yl)propanoyl]piperidin-4-yl}-4-(3,4-dimethoxyphenyl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one hydrochloride [ No CAS ]
  • 18
  • [ 71239-85-5 ]
  • [ 1416467-42-9 ]
  • 19
  • [ 71239-85-5 ]
  • [ 1416467-43-0 ]
  • 20
  • (4aS,8aR)-4-(3,4-dimethoxyphenyl)-2-(piperidin-4-yl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one hydrochloride [ No CAS ]
  • [ 71239-85-5 ]
  • [ 1416468-93-3 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1.5h; B63. tert-Butyl [(2S)-1 -{4-[(4aS,8aR)-4-(3,4-dimethoxyphenyl)-1 -oxo-4a,5,6,7,8,8a- hexahydrophthalazin-2(1 H)-yl]piperidin-1 -yl}-1 -oxo-3-(pyridin-2-yl)propan-2- yl]carbamate; To a suspension of (4aS,8aR)-4-(3,4-dimethoxyphenyl)-2-(piperidin-4-yl)-4a,5,6,7,8,8a- hexahydrophthalazin-1 (2H)-one hydrochloride (1.02 g; compound B76), N-(tert-butoxycarbonyl)-3- pyridin-2-yl-L-alanine (666 mg) and HBTU (1.04 g) in DCM (15 ml) was added DIPEA (1.7 ml) and the mixture was stirred for 1.5 h at RT. Afterwards the mixture was extracted with saturated aqueous so- dium bicarbonate solution (10 ml), the organic layer was separated and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by flash column chromatography [silica gel, eluation gradient: EtOAc/MeOH, 95/5 to 90/10 (v/v)] to yield the title compound as a solid. MS: calc: Cs^sNsOe (619.75) found: [MH+] = 620.2
  • 21
  • [ 1470000-35-1 ]
  • [ 71239-85-5 ]
  • [ 1470000-24-8 ]
  • 22
  • [ 1470000-35-1 ]
  • [ 71239-85-5 ]
  • [ 1470000-18-0 ]
YieldReaction ConditionsOperation in experiment
86% With caesium carbonate; In butanone; at 110℃; for 72.0h;Sealed tube; General procedure: The appropriate Boc-amino acid (0.16mmol, 1eq.) and cesium carbonate (0.16mmol, 1eq.) were added to a solution of the 7alpha-(E)-4-chlorobut-2-enyl-4-androsten-17beta-ol-3-one acetate (11) (0.16mmol, 1eq.) in butan-2-one (2mL). The key intermediate 7alpha-(E)-4-chlorobut-2-enyl-4-androsten-17beta-ol-3-one acetate (11) was efficiently prepared as described in an earlier study [37-41]. The reaction mixture was heated to 110C under pressure in sealed tube and stirred for 3 days. Afterwardthe mixture was cooled to room temperature, the solvent was evaporated under reduced pressure. The residue was solubilized by methylene chloride (15mL) and washed with a solution of sodium hydroxide 1N (15mL). The aqueous phase was extracted thrice with methylene chloride (15mL). The combined organic phases were washed with brine (25mL), dried over anhydrous sodium sulfate, filtered, and evaporated to dryness under vacuum. The crude compound was purified by flash chromatography on silica gel to afford compounds 8a-f.
  • 23
  • [ 204387-54-2 ]
  • [ 71239-85-5 ]
  • [ 1580457-01-7 ]
YieldReaction ConditionsOperation in experiment
General procedure: Asolution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-(furan-3-yl)propanoicacid (compound 12a, 105 mg, 0.410 mmol) in DMF (5 mL) was added HATU(283 mg, 0.745 mmol) and DIPEA (96 mg, 0.745 mmol). After stirring for 30 mincompound 11 (100 mg, 0.373 mmol) andadditional DIPEA were added. This solution was allowed to stir at roomtemperature for 20 h and then the saturated NaHCO3 was added. Themixture was extracted with EtOAc and washed with saturated NaCl, dried over Na2SO4and concentrated. The residue was purified with flash chromatography on silicagel, eluted with a mixture of PE/EA (4/1, v/v) to afford 13a (105 mg, 85%) as a white solid.
  • 24
  • [ 666748-56-7 ]
  • [ 71239-85-5 ]
  • [ 1416468-93-3 ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 1.5h; To a suspension of (4aS,8aR)-4-(3,4-dimethoxyphenyl)-2-(piperidin-4-yl)-4a,5,6,7,8,8a-hexahydrophthalazin-1(2H)-one hydrochloride (1.02 g; compound B76), <strong>[71239-85-5]N-(tert-butoxycarbonyl)-3-pyridin-2-yl-L-alanine</strong> (666 mg) and HBTU (1.04 g) in DCM (15 ml) was added DIPEA (1.7 ml) and the mixture was stirred for 1.5 h at RT. Afterwards the mixture was extracted with saturated aqueous sodium bicarbonate solution (10 ml), the organic layer was separated and dried over sodium sulfate. The organic layer was concentrated under reduced pressure and the residue was purified by flash column chromatography [silica gel, eluation gradient: EtOAc/MeOH, 95/5 to 90/10 (v/v)] to yield the title compound as a solid. [0602] MS: calc.: C34H45N5O6 (619.75) found: [MH+]=620.2
  • 25
  • [ 71239-85-5 ]
  • [ 1416468-46-6 ]
  • 26
  • [ 71239-85-5 ]
  • (2S)-2-amino-3-(pyridin-2-yl)propan-1-ol [ No CAS ]
  • 27
  • [ 71239-85-5 ]
  • (2S)-2-(benzylamino)-3-(pyridin-2-yl)propan-1-ol [ No CAS ]
  • 28
  • [ 71086-99-2 ]
  • [ 71239-85-5 ]
  • C24H28N4O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; trichlorophosphate; In dichloromethane; at -10℃; for 2.0h; General procedure: To amixture of Boc-Phe-OH (33a) (5 g, 18.9 mmol), ethyl 5-amino-1H-indole-2-carboxylate (34) (3.9 g,18.9 mmol) and pyridine (5 mL) in CH2Cl2 (50 mL) at -10 C was added POCl3 (2.9 g, 18.9 mmol)dropwise. After addition, the reaction mixture was stirred at 10 C for 2 h when TLC analysisindicated completion of reaction, then H2O (10 mL) was added and the organic layer was separated,washed by hydrochloric acid (1 M, 10 mL), dried by Na2SO4, filtered. The filtrate was evaporated invacuum to get crude 35a as a brown solid, which was used for next step without further purification(6.6 g, 77.6% yield).
  • 29
  • [ 2577-90-4 ]
  • [ 71239-85-5 ]
  • C23H29N3O5 [ No CAS ]
  • 30
  • [ 71239-85-5 ]
  • Leu-Phe-OMe trifluoroacetate [ No CAS ]
  • C29H40N4O6 [ No CAS ]
 

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