26531-82-8|Methyl (S)-2-amino-2-(4-hydroxyphenyl)acetate| Ambeed

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CAS No. :	26531-82-8
Formula :	C₉H₁₁NO₃
M.W :	181.19
SMILES Code :	O=C(OC)[C@@H](N)C1=CC=C(O)C=C1
MDL No. :	MFCD08669794
InChI Key :	SZBDOFWNZVHVGR-QMMMGPOBSA-N
Pubchem ID :	10932044

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

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 20℃; for 12h;Inert atmosphere;	To a solution of (S)-2-amino-2-(4-hydroxyphenyl)acetic acid (15.0 g, 89.7 mmol, CAS 228 18-40-2) in methanol (100 mL) was added thionyl chloride (21.3 g, 179 mmol, 13 mL). The mixture was stirred at rt for 12 hours. The reaction mixture was concentrated under vacuum to give the title compound. LCMS: (ESj m/z (M+H) = 182.1, tR = 0.690.
	With acetyl chloride; at 0 - 40℃; for 18h;	To a solution of 20 ML (230 mmol) of acetyl chloride in 400 ML of methanol at 0 °C was added 20 g (120 mmol) of (S)-4-HYDROXYPHENYLGLYCINE. The mixture was stirred at ambient temperature for 16 h, heated at 40 °C for 2 h, cooled and concentrated in vacuo. Water was added and the mixture was extracted with three portions of dichloromethane. The combined organic phase was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give the crude methyl ester. This material was dissolved in 400 mL of dichloromethane and 28.8 g (132 mmol) of di-tert-butyl dicarbonate, and 31.4 mL (180 mmol) OF N, N-DIISOPROPYLETHYLAMINE (DIEA) was added. The mixture was stirred at ambient temperature for 20 h, concentrated in vacuo, and dissolved in 400 ML of ethyl acetate. The organic phase was washed with sequentially with saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, and concentrated in vacuo. The crude solid was triturated with 200 mL of 1: 4 ether : hexane to give 30 g of the Boc carbamate which was dissolved in 300 ML of acetic acid. To the solution was added 2.2 g of platinum (IV) oxide and the reaction was shaken under an atmosphere of hydrogen (48 psi) for 2 h, filtered and concentrated in vacuo. The crude material was dissolved in ethyl acetate and washed sequentially with saturated sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, and concentrated in vacuo. Purification by flash chromatography (silica gel, 20 to 40percent ethyl acetate in hexanes) afforded 8.83 g of the cis title compound: 1H NMR (400 MHz, CDC13) 8 5.05 (bd, 1H, J = 12HZ), 4.33-4. 27 (M, 1H), 4.05 (bs, 1H), 3.78 (s, 3H), 1.89-1. 78 (M, 2H), 1. 63-1. 38 (M, 16H). Continued elution gave 3.50 g of the trans title compound: H NMR (400 MHz, CDC13) 5 5.04 (bd, 1H, J = 12HZ), 4.30-4. 23 (M, 1H), 3.78 (s, 3H), 3.59-3. 51 (M, 1H), 2. 08-2. 00 (M, 2H), 1.79-1. 50 (M, 3H), 1.43 (s, 9H), 1.33-1. 04 (M, 4H).

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CAS No.: 26531-82-8

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CAS No.: 26531-82-8

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[ 26531-82-8 ] Synthesis Path-Downstream 1~4

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Physical hazards
Code	Phrase
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
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed