183793-47-7|Benzyl N-(tert-butoxycarbonyl)-O-methyl-L-serinate| Ambeed

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CAS No. :	183793-47-7
Formula :	C₁₆H₂₃NO₅
M.W :	309.36
SMILES Code :	O=C(OCC1=CC=CC=C1)[C@H](COC)NC(OC(C)(C)C)=O

Yield	Reaction Conditions	Operation in experiment
	With dmap; triethylamine; In dichloromethane; at 0℃; for 3.5h;	To a 0° C. solution of N-Boc serine(methyl ether)-OH (43.8 g, 200 mmol), triethylamine (26.5 g, 260 mmol) and 4-(dimethylamino)pyridine in dichloromethane (1.2 L) was added a solution of benzyl chloroformate (41 g, 240 mmol) in dichloromethane (250 mL) over 30 minutes and the resulting mixture was stirred at the same temperature for another 3 hours. Saturated aqueous sodium bicarbonate (200 mL) was then added and the organic layer was washed with saturated aqueous sodium bicarbonate (200 mL) and brine (200 mL). The organic layers were dried over sodium sulfate and filtered through Celite-545. The solvents were removed under reduced pressure and residue was purified by flash chromatography (hexane and ethyl acetate) to provide (076) (54 g) which was characterized by LC/MS (LCRS (MH) m/z: 310.16).
	With triethylamine; In dichloromethane; at 0℃; for 3.5h;	Example 1; Synthesis of Compound 1; Synthesis of (A); To a 0° C. solution of N-Boc serine(methyl ether) (43.8 g, 200 mmol), triethylamine (26.5 g, 260 mmol) and 4-(dimethylamino)pyridine in dichloromethane (1.2 L) was added a solution of benzyl chloroformate (41 g, 240 mmol) in dichloromethane (250 mL) over 30 minutes. The resulting mixture was stirred at the same temperature for another 3 hours. Saturated aqueous sodium bicarbonate (200 mL) was added and organic layer was separated, the residual mixture was extracted with dichloromethane (2.x.400 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (200 mL) and brine (200 mL), dried over sodium sulfate and filtered through Celite-545. The solvents were removed under reduced pressure and residue was purified by flash chromatography (silica gel, hexane and ethyl acetate). Compound (A) (54 g) was isolated and characterized by LC/MS (LRMS (MH) m/z: 310.16).
54 g	With dmap; triethylamine; In dichloromethane; at 0℃; for 3.5h;	To a 00 C. solution of N-Hoc serine(methyl ether) (43.8 g, 200 mmol), triethylamine (26.5 g, 260 mmol) and 4-(dimethylamino)pyridine in dichloromethane (1.2 L) was added a solution ofbenzyl chloroformate (41 g, 240 mmol) in dichloromethane (250 mE) over 30 minutes. The resulting mixture was stirred at the same temperature for another 3hours. Saturated aqueous sodium bicarbonate (200 ml) was added and organic layer was separated, the residual mixture was extracted with dichloromethane (2x400 mE). The combined organic layers were washed with saturated aqueous sodium bicarbonate (200 mE) and brine (200 mE), dried over sodium sulfate and filtered through Celite-545. The solvents were removed under reduced pressure and residue was punrified by flash chromatography (silica gel, hexane and ethyl acetate). Compound (A) (54 g) was isolated and characterized by LC/MS (LRMS (MH) mlz: 310.16).

	With dmap; triethylamine; In dichloromethane; at -5℃; for 3h;Inert atmosphere;	L) To a solution of Boc-methylserine (13) in DCM (Dichlormethane) TEA (Triethylamine) and DMAP (4-Dimethylaminopyridine) are added. The resulting solution is cooled to -5 °C, and benzyl chloroformate is then slowly added via an addition funnel under an atmosphere of argon. The reaction is kept at the same temperature for 3 h and then diluted with brine. The layers are separated, and the aqueous layer is extracted with DCM. The organic layers are combined and dried over Na2S04- The Na2S04 is removed by filtration, and the volatiles are removed under reduced pressure. The resulting residue is purified by flash chromatography using a mixture of hexane and ethyl acetate to provide intermediate (14) as white solid.
54 g	With dmap; triethylamine; In dichloromethane; at 0℃; for 3.5h;	To a 0°C. solution of N-Boc serine(methyl ether) (43.8 g, 200 mmol), triethylamine (26.5 g, 260 mmol) and 4-(dimethylamino)pyridine in dichloromethane (1.2 L) was added a solution of benzyl chloroformate (41 g, 240 mmol) in dichloromethane (250 mE) over 30 minutes. The resulting mixture was stirred at the same temperature for another 3 hours. Saturated aqueous sodium bicarbonate (200 mE) was added and organic layer was separated, the residual mixture was extracted with dichloromethane (2x400 mE). The combined organic layers were washed with saturated aqueous sodium bicarbonate (200 mE) and brine (200 mE), dried over sodium sulfate and filtered through Celite-545. The solvents were removed under reduced pressure and residue was purified by flash chromatography (silica gel, hexane and ethyl acetate). Compound (A) (54 g) was isolated and characterized by LC/MS (LRMS (MH) mlz: 310.16).
54 g	With dmap; triethylamine; In dichloromethane; at 0℃; for 3.5h;	To a 0° C. solution of N-Boc serine(methyl ether) (43.8 g, 200 mmol), triethylamine (26.5 g, 260 mmol) and 4-(dimethylamino)pyridine in dichloromethane (1.2 L) was added a solution of benzyl chloroformate (41 g, 240 mmol) in dichloromethane (250 mL) over 30 minutes. The resulting mixture was stirred at the same temperature for another 3 hours. Saturated aqueous sodium bicarbonate (200 mL) was added and organic layer was separated, the residual mixture was extracted with dichloromethane (2×400 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (200 mL) and brine (200 mL), dried over sodium sulfate and filtered through Celite-545. The solvents were removed under reduced pressure and residue was purified by flash chromatography (silica gel, hexane and ethyl acetate). Compound (A) (54 g) was isolated and characterized by LC/MS (LRMS(MH) m/z: 310.16).

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CAS No.: 183793-47-7

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CAS No.: 183793-47-7

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[ 183793-47-7 ] Synthesis Path-Downstream 1~2

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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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
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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
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