83623-93-2|(2S,4S)-1-(tert-Butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid| Ambeed

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CAS No. :	83623-93-2
Formula :	C₁₁H₁₉NO₅
M.W :	245.27
SMILES Code :	O=C([C@H]1N(C(OC(C)(C)C)=O)C[C@@H](OC)C1)O
MDL No. :	MFCD11501217
InChI Key :	COHIMMPWCAHSFN-YUMQZZPRSA-N
Pubchem ID :	15222286

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

Yield	Reaction Conditions	Operation in experiment
95.8%	With water; sodium hydroxide; In methanol; at 60℃; for 8h;	At room temperature, compound BB-29-2 (5.5 g, 21.3 mmol) was dissolved in a mixed solvent of methanol/H2O (30 mL/30 mL), NaOH (1.7 g, 42.6 mmol) was added. The reaction system was heated to 60 C. and stirred for 8 h. After the reaction was complete as detected by TLC, most solvent was removed under reduced pressure and then the mixture was cooled to 0 C. 2N Hydrochloric acid was dripped to adjust pH to 3-4, the mixture was extracted with ethyl acetate (80 mL×3). The organic phases were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated by a rotary evaporator to remove the solvent thereby delivering the target compound BB-29-3 (yellow oil, 5.0 g, yield 95.8%). The product was directly used for the next step without purification. 1H NMR (CDCl3, 400 MHz): δ 4.42-4.14 (m, 1H), 3.99-3.98 (m, 1H), 3.65-3.53 (m, 2H), 3.33 (s, 3H). 2.31-2.05 (m, 2H), 1.47 (s, 9H).
		(2) Synthesis of (2S,4S)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid According to the manner similar to that of Example 6(2), the title compound (310 mg) was obtained as a colorless solid from methyl (2S,4S)-1-(tert-butoxycarbonyl)-4-methoxypyrrolidine-2-carboxylate (350 mg). This intermediate was used for the next reaction without purification.
		1 M LiOH (15 ml, 15 mmol) was added to a solution of methyl ester BB42-a (1.96 g, 7.57 mmol) in THF (15 ml) and the resulting mixture was stirred for at room temperature 5h. The pH of the reaction mixture was adjusted to 5 by addition of 1 N HCI whereafter the mixture was extracted with EtOAc (4x50 ml), dried (Na2S04), filtered and concentrated under reduced pressure which gave the title compound (1.85 g, 100%) which was used without further purification in the next step. MS (ESI):246[M+H]+.

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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P370 + P378	In case of fire:
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Disposal
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CAS No.: 83623-93-2

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CAS No.: 83623-93-2

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[ 83623-93-2 ] Synthesis Path-Downstream 1~1

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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