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CAS No. :	55750-63-5
Formula :	C₁₄H₁₆N₂O₆
M.W :	308.29
SMILES Code :	O=C(ON1C(CCC1=O)=O)CCCCCN2C(C=CC2=O)=O
Synonyms :	EMCS
MDL No. :	MFCD00043043
InChI Key :	VLARLSIGSPVYHX-UHFFFAOYSA-N
Pubchem ID :	5091655

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
97%	With triethylamine; In N,N-dimethyl-formamide; at 20℃;	150 mg (0.797 mmol) of <strong>[1115-74-8]L-valyl-L-alanine</strong> and 246 mg (0.797 mmol) of 1-{6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexyl}-1H-pyrrole-2,5-dione were dissolved in 4.0 ml of dimethylformamide, and 0.220 ml (1.6 mmol) of triethylamine was added. The reaction mixture was stirred at RT overnight. The reaction mixture was purified directly by preparative RP-HPLC (column: Reprosil 250*30; 10mu, flow rate; 50 ml/min, MeCN/water). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 302 mg (97% of theory) of N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl) hexanoyl]-<strong>[1115-74-8]L-valyl-L-alanine</strong>. LC-MS (Method 12): Rt=1.02 min; MS (ESIpos): m/z=382 (M+H)+. 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=0.82 (dd, 6H), 1.17 (m, 2H), 1.27 (d, 3H), 1.48 (m, 4H), 1.94 (m, 1H), 2.13 (m, 2H), 3.38 (t, 2H), 4.17 (m, 2H), 7.00 (s, 2H), 7.75 (d, 1H), 8.19 (d, 1H).
70%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Maeilimidocaproy. N-hydroxysuccinimide (1.619 g, 5.25 mmo., 105 eq.) and H-Val-Aia-OH (0,941 g, 5 mmol, 1 eq.) were placed in a 25 ml recovery fiask with a stir bar and the flask was flushed with nitrogen, DMF (4,7 mL) was added and the resulting white siurry was stirred. DIPEA (0.87 mL, 5 mmol, 1 eq) was added and the mixture was allowed to stir at room temperature overnight. The mixture was coo.ed in an ice/water bath and 2M HCI (3 mL, 6 mmol) was added dropwise. The viscous mixture was transferred to a separator/ funnel and the reaction vessel rinsed with sat. NaCl (7 mL), EtOAc (10 mL), sat NaCl {10 mL) and EtOAc (5 mL). After separation of the aqueous phase, it was extracted with additionai EtOAc {2 x 15 mL). The combined organic extracts were washed with sat NaCi {4 x 15 mL), until the washings were pH ~3,5. The organic extracts were dried over Na2S04, filtered and concentrated under reduced pressure to give crude 5 as a white solid (2,1 2 g, 114% crude yield). Crude 5 was suspended in warm CHjCIa {35 mL) and filtered to remov a fine white solid. The solids wer rinsed with additional CHjCi2 (3 mL). Toiuene {5mL) was added and the mixture was cooled in an ice/water bath, which resulted in a thick siurry. The solids were collected by filtration, washed with a cold mixture of CHjC (12 mL) and toluene (2 mL) and dried by puiilng air through the sample overnight to give 5 as a White solid (1 ,327 g, 70% yield). TLC: Rf = 0.26, 10% MeOH in CH2CI2. 1 H NMR (CDCI3)(ppm) 0.95 {d, J - 17 Hz, 3H), 0.98 (d, J - 17 Hz, 3H), 1.30 (m, 2H), 1.40 (d, J = 17 Hz, 3H), 1.61 (m, 4H), 2.06 (m, 1 H), 2.25 (dt, J = 4, 19 Hz, 2H). 3.35 (s, 1 H), 3.49 (t, J - 17 Hz,2H), 4.20 (d, J = 18 Hz, 1 H), 4.38 (m, 1 H), 6.80 {s, 2H). Analytical HPLC (0.1% formic acid): tR 9.05 min. LC-MS: tR 11.17 min, m/z (ES+) found 381.9 (M+H)+, m/z (ES-) found 379.9 (M-H)-.
52%	In N,N-dimethyl-formamide; at 20℃; for 48h;	(a) (S)-2-((S)-2-(6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanamido)-3- methylbutanamido)propanoic acid (23)A suspension of dipeptide (22) (0.1 g, 0.54 mmol, 1 eq.) and 6-maleimidohexanoic acid succinimide ester (0.165 g, 0.54 mmol, 1 eq.) in anhydrous DMF (5 mL) was stirred at room temperature for 24 hours at which time LCMS indicated 50% conversion to a new product. The reaction mixture was diluted with anhydrous DMF (5 mL) and the reaction was allowed to continue for a further 24 hours. The solvent was evaporated under reduced pressure to give a colourless residue. Diethyl ether (60 mL) was added and the mixture was sonicated for 5 min, the ether was decanted and the process was repeated (x 2). The final ethereal portion was filtered to isolate the product (23) as a white powder which was dried under vacuum (0.105 g, 52%). Analytical Data: RT 2.28 min; MS (ES+) m/z (relative intensity) 382 ([M + H]+ , 90), MS (ES") m/z (relative intensity) 380 ([M - H])-, 100).

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P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
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Code	Phrase
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P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Disposal
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P501	Dispose of contents/container to ...
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CAS No.: 55750-63-5

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CAS No.: 55750-63-5

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[ 55750-63-5 ] 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