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CAS No. : | 167102-61-6 | MDL No. : | MFCD11041265 |
Formula : | C10H20N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 248.28 | Pubchem ID : | 11032217 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | - | H-Bond Acceptor Count : | - |
XLogP3 : | - | H-Bond Donor Count : | - |
SP3 : | - | Rotatable Bond Count : | - |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15℃; for 1.0h; | [0117] To a solution of Boc-D-Ser-OH (5 g, 24.37 mmol) in anhydrous DCM (100 mL) at -15C were added N,O-dimethylhydroxylaminehydrochloride (2.54 g, 26.07 mmol) and N-methylmorpholine (2.87 mL, 26.07 mmol). N-(3-Dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (5.00 g, 26.07 mmol) was then added portionwise (5 portions) over 20min. The mixture was stirred at -15C for 40 min. A 1 M HCl solution (50 mL) was added. The mixture was extractedwith DCM (2 x 25 mL). The organic layer was washed with a saturated solution of NaHCO3 (50 mL), H2O (50 mL), driedover Na2SO4 and concentrated in vacuo to provide the tert-butyl N-[(1R)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate (5a) (5.42 g, 21.83 mmol, 89%) as a white solid.1H NMR (400 MHz, CDCl3) delta 1.44 (s, 9H), 2.65 (s, 1 H), 3.23 (s, 3H), 3.62-3.97 (m, 5H), 4.79 (s, 1 H), 5.60 (d, J = 8.4 Hz, 1H). |
83% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 20.5h;pH 4.5;Cooling with ice; | Boc-D-Serine (25.5 g, 124.5 mmol, 1.0 equiv.) was dissolved intetrahydrofuran (112 niL) and N,0-dimethylhydroxylamine hydrochloride (14 g, 143.3 mmol, 1.2 equiv.) in water (112 mL) was added. While cooling in an ice bath, IN sodium hydroxide was added to bring the pH to 4.5, then sodium hydroxide (2.45 g, 61.2 mmol, 0.5 equiv.) in water (329 mL) was added to maintain pH 4.5 and a solution of N-ethyl-N-(3-dimethylaminopropyl)carbodiimide hydrochloride (27.8 g, 145.0 mmol, 1.2 equiv.) in water (281 mL) was slowly added during 30 min (the reaction was monitored by pH meter). After stirring for 20 h at r.t., the solution was saturated with sodium chloride and extracted 3x with ethyl acetate (201 mL).Combined organic extracts were concentrated to give a crude solid. The solid was dissolved in ethyl acetate with the help of the heating and hexanes were added to give a light orange solution. As the solution cooled, small colorless crystals started forming. The solution was allowed to stand at r.t. for 30 min before being placed in an ice-bath for 30 min. The resulting colorless crystals were filtered and rinsed with 10% ethyl acetate/hexanes and dried in air to afford the title compound as a shiny snow-flakes like solid (16.48 g). The filtrate was concentrated and recrystallized to give the second crop (9.03 g) as a white solid, (total 25.5 g, 83%). NMR (300 MHz, CDCI3), delta 5.56 (brs, 1H), 4.80 (brs, 1H), 3.83 - 3.78 (m, 5H), 3.23 (s, 3H), 2.52 (brs, 1H), 1.45 (s, 9H). |
77% | With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15℃; for 2.16667h;Inert atmosphere; | Scheme 1Example 1N-{2-[(3S)-3-{[(4-aminophenyl)su.fo^ phenyl}- N -(methoxycarbonyl)-p-phenyl-L-phenylalaninamide ( 12)Step 1 : A^-(^/-butoxycarbonyl)-N-methoxy-iV-inethyl-D-seriDamide (1) A suspension of N-(rert-butoxycarbonyl)-D-serine (2.06 g, 10.05 mol) in dry DCM(40 ml), stirred at -15 C (ice/salt bath) under N2 atmosphere was treated with solid N,0 hydroxylamine hydrochloride ( 1.104 g, 11 mmol) followed by N-methylmorpholine ( 1.202g, 11.9 mmol). EDC (2011 mg, 10.49 mmol) was then added to the reaction flask in five equal portions over the first 40 min, after completely charged with EDC, the reaction mixture was further stirred at the same temperature for extra 1.5h. Diluted with DCM, washed with aqueous 5% KHS04 followed by saturated solution of NaHC03, dried over Na2S04 and stored under vacuum to give 1.93g (7.78 mmol, 77% yield) of the title compound as a white solid. MS : m/z= 271.1 (MNa+). |
73% | With 4-methyl-morpholine; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at -15℃; for 1.5h; | (R)-2- (tert-butoxycarbonyl)-3-hydroxypropanoic acid (5.0 g, 24.4 mmol, 1.0 equiv. ) was added to a 250 mL RBF followed by CH2C12 (90 mL) and cooled to-15 C via an ice/salt water bath. Next, N, O- dimethylhydroxyl amine-HCl (2.5 g, 25.6 mmol, 1.1 equiv. ) and N methylmorpholine (2.8 mL, 25.6 mmol, 1.1 equiv) were added to the reaction flask. EDC (4.9 g, 25.6 mmol, 1.1 equiv. ) was then added to the reaction flask in 5 equal portions over the first 30 min (1 portion per 6 min). After completely charged with EDC, the reaction was allowed to stir an additional 1 h at-15 C. The reaction was quenched with ice cold 1% HCl (25 mL) and transferred to a separatory funnel with CH2Cl2 (100 mL). The mixture was washed with 1% HCl (3 x 30 mL), sat. NaHCO3 (2 x 30 mL), and sat. NaCl (1 x 30 mL). The organic layer was separated and dried over Na2S04. The solution was concentrated on a rotary evaporator and dried under vacuum to give 4.4 g (73%) of 21 as a white solid. Rif= 0. 36 (100% EtOAc); mp = 115- 116 C ; [a] D23. s-+13. 3 (c 1.00, MeOH) ; IR (KBr) 3470,3354, 2977,2943, 1703,1645, 1538,1363, 1180, 1078, 1064 cm-1; 1H NMR (500 MHz, CDCl3) No. 5.66 (br d, J= 6.0 Hz, 1H, carbamate-NH), 4.81 (br s, 1H, Boc-NH-CH), 3.82 (m, 2H, CH-CH), 3.79 (s, 3H, N-OCH3), 3.24 (s, 3H, N-CH3), 2.86 (br s, 1H, CH2-OH), 1.45 (s, 9H, t-butyl-CH3) ; 13C (125 MHz, CDC13) 8 171.1, 156. 1, 80.2, 63.9, 61.8, 52.6, 32.3, 28.5 ; LRMS (ESI-MS mlz) : Mass calcd for CloH20N2o5 [M] +, 248.28. Found 249. Spectroscopic data were consistent with the literature data for this compound. |
92 g | With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at -15 - -10℃; for 2.0h;Inert atmosphere; | (i?)-2-((feri-Butoxycarbonyl)amino)-3-hydroxypropanoic acid (100 gms) was added to dichloromethane (1000 ml) under nitrogen atmosphere and stirred for 10-15 min at 25-30C. Cooled the reaction mixture to -15 to -10C. N, O-Dimethylhydroxylamine hydrochloride (45.4 gms), N-methylmorpholine (123.2 gms) and l-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (95.2 gms) were added and stirred the reaction mixture for 2 hr at -15 to -10C. Acidified the reaction mixture with IN hydrochloric acid solution (600 ml) and stirred for 15 min. Separated the both aqueous and organic layers. Basify the organic layer with 5% aqueous sodium bicarbonate solution and stirred for 15 min. Separated the organic and aqueous layers and distilled off the solvent completely from the organic layer under reduced pressure. Petroleum ether ( 100 ml) was added to the above obtained material at 25- 30C and stirred the reaction mixture for 60 min at same temperature. Filtered the precipitated solid and dried to get the title compound. (Yield: 92.0 gms) |
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