106928-50-1|Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate| Ambeed

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CAS No. :	106928-50-1
Formula :	C₁₁H₁₉NO₄
M.W :	229.27
SMILES Code :	C=CCC(NC(OC(C)(C)C)=O)C(OC)=O
MDL No. :	MFCD10687067

Yield	Reaction Conditions	Operation in experiment
94%		A solution of di-tert-butyl dicarbonate (11.4 g, 52.1 mmol) in 1,4-dioxane (15 mL) was slowly added to a second solution of 2-amino-5-pentenoic acid (5 g, 43.4 mmol) in 1 N NAOH (55 mL) at 0 C. After stirring for 16h, the solution was acidified with 5% HC1 to pH 2, and the resulting mixture was extracted with ethyl acetate (3 x 80 mL). The combined organic layers were dried OVER MGS04 and concentrated. The resulting residue was dissolved in DMF (50 mL) and treated with K2CO3 (7 g, 51 MMOL). After stirring for 15 min, the solution was cooled to 0 C and treated with iodomethane (3.4 mL, 51 mmol). After the addition was complete, the reaction mixture was stirred at room temperature for another 4 h, filtered and the resulting solid was washed with ethyl acetate (200 mL). The filtrate was washed successively with 5% aq HC1, sat. aq NaCl, dried over MGS04 and concented. Purification by flash column chromatography (5% ethyl acetate in heptane) provided 2-tert-Butoxycarbonylamino-5-pentenoic acid methyl ester (9.03 g, 94%) as an oil. 1H NMR (CDC13), 5.73 (m, 1 H), 5.12 (m, 1 H), 5.03 (m, 1 H), 4.38 (dd, J = 6, 12 Hz, 1 H), 3.74 (s, 3 H), 2.51 (m, 2 H), 1.46 (s, 9 H).
79%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃; for 7h;	Methyl N-Boc-2-aminopent-4-enoic acid (250mg, 1.163mmol) was dissolved in dry DMF (3mL) and K2CO3 (241mg, 1.744mmol) was added. The suspension was cooled to 0C and methyl iodide (330mg, 2.326mmol) was added slowly with stirring. Stirring was continued at 0C for 3h and at r.t. for 4 more hours. Water (70mL) was added and the solution was extracted with ethyl acetate (3×25mL). The combined organic layers were washed with brine (2×25mL) and dried (MgSO4). The solvent was evaporated to give a light brownish oil. Yield: 210mg (79%). 1H NMR (CDCl3): δ 1.44 (s, 9H, CH3), 2.51 (br m, 2H, H-3), 3.74 (s, 3H, OCH3), 4.38 (br m, 1H, NH), 5.03 (br m, 1 H, H-2), 5.07 (s, 1H, H-5cis), 5.10 (m, 1H, H-5trans), 5.65 (m, 1H, H-4), 13C NMR (CDCl3): δ 28.3 (q, CH3), 36.7 (t, C-3), 52.0 (d, C-2), 52.8 (q, OCH3), 79.7 (s, O-C), 118.9 (t, C-5), 132.3 (d, C-4), 155.1 (s, Boc), 172.4 (s, C-1).
	With potassium carbonate; In acetone; for 4h;Reflux;	2-tert-Butoxycarbonylamino-pent-4-enoic acid (9.3 g, 43.3 mmol) in acetone (70 mL) is treated with solid potassium carbonate (11.9 g, 86.6 mmol) followed by methyl iodide (5.4 mL, 86.6 mmol). The resulting mixture is heated to reflux for 4 h and then allowed to cool to RT. The solvent is removed in vacuo and the crude residue is dissolved in EtOAc, washed with water, saturated sodium hydrogen carbonate solution, brine, dried (MgSO4) and concentrated in vacuo. The crude residue is purified by flash chromatography (SiCh, zso-hexane:EtOAc 7:3) to afford the title compound as a light-yellow oil.

Yield	Reaction Conditions	Operation in experiment
	With methanol; In hexane; dichloromethane; at 20℃; for 3h;	(2) Trimethylsilyldiazomethane (2N, in hexane) (12 ml) was added dropwise to a solution of<strong>[119479-32-2]N-Boc-allylglycine</strong> (3.09 g) in dichloromethane/methanol (2/1) mixture (30 ml), and the resulting mixture was stirred at room temperature for 3 hours. After concentrating the reaction solution, the residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate = 20/1→10/1) to obtain <strong>[119479-32-2]N-Boc-allylglycine</strong> methyl ester (3.11 g). NMR(H1, CDC13):δ 2.43-2.55(2H, m), 3.72(3H, s), 4.34-4.39(1H, brm), 5.02(1H, brs), 5.09-5.13(2H, m), 5.62-5.72(1H, m)
	In methanol; hexane; dichloromethane; at 20℃; for 3h;	Trimethylsilyldiazomethane (2N, in hexane) (12 ml) was added dropwise to a solution of <strong>[119479-32-2]N-Boc-allylglycine</strong> (3.09 g) in dichloromethane/methanol (2/1) mixture (30 ml), and the resulting mixture was stirred at room temperature for 3 hours. After concentrating the reaction solution, the residue was purified by column chromatography (silica gel, eluent: cyclohexane/ethyl acetate = 20/1→10/1) to obtain <strong>[119479-32-2]N-Boc-allylglycine</strong> methyl ester (3.11 g). NMR(H1, CDCl3):δ 2.43-2.55(2H, m), 3.72(3H, s), 4.34-4.39(1H, brm), 5.02(1H, brs), 5.09-5.13(2H, m), 5.62-5.72(1H, m)

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CAS No.: 106928-50-1

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CAS No.: 106928-50-1

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[ 106928-50-1 ] Synthesis Path-Downstream 1~3

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
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H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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