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Chemical Structure| 16395-58-7

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Product Details of [ 16395-58-7 ]

CAS No. :16395-58-7
Formula : C7H12N2O2
M.W : 156.18
SMILES Code : O=C([C@H]1N(C(C)=O)CCC1)N
MDL No. :MFCD00037340
InChI Key :CXURPNUIYCJENH-LURJTMIESA-N
Pubchem ID :85395

Safety of [ 16395-58-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Application In Synthesis of [ 16395-58-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 16395-58-7 ]

[ 16395-58-7 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 600-18-0 ]
  • [ 16395-58-7 ]
  • (Z)-Ac-Pro-Δ-Leu [ No CAS ]
  • (E)-Ac-Pro-ΔAbu [ No CAS ]
  • 2
  • [ 816-66-0 ]
  • [ 16395-58-7 ]
  • (Z)-Ac-Pro-ΔLeu [ No CAS ]
  • 3
  • [ 759-05-7 ]
  • [ 16395-58-7 ]
  • Ac-Pro-Δ-Val [ No CAS ]
  • 4
  • [ 156-06-9 ]
  • [ 16395-58-7 ]
  • Ac-Pro-(Z)-Δ-Phe [ No CAS ]
  • 5
  • [ 16395-58-7 ]
  • [ 127-17-3 ]
  • Ac-Pro-Δ-Ala [ No CAS ]
  • 6
  • [ 108-05-4 ]
  • [ 7531-52-4 ]
  • [ 16395-58-7 ]
  • 7
  • [ 108-24-7 ]
  • [ 147-85-3 ]
  • [ 16395-58-7 ]
  • 8
  • [ 75-36-5 ]
  • [ 7531-52-4 ]
  • [ 16395-58-7 ]
  • 9
  • [ 16395-58-7 ]
  • C7H11N2O2 [ No CAS ]
  • 10
  • [ 16395-58-7 ]
  • Ac-Pro-Δ-Ala-NHMe [ No CAS ]
  • 11
  • [ 16395-58-7 ]
  • Ac-Pro-Δ-Val-NHMe [ No CAS ]
  • 12
  • [ 16395-58-7 ]
  • C17H26N2O6 [ No CAS ]
  • 13
  • [ 16395-58-7 ]
  • C21H26N2O6 [ No CAS ]
  • 14
  • [ 16395-58-7 ]
  • Ac-Pro-(Z)-Δ-Phe-NHMe [ No CAS ]
  • 15
  • [ 16395-58-7 ]
  • (S)-1-Acetyl-pyrrolidine-2-carboxylic acid [1-methylcarbamoyl-prop-(Z)-ylidene]-amide [ No CAS ]
  • 16
  • [ 16395-58-7 ]
  • (S)-1-Acetyl-pyrrolidine-2-carboxylic acid [3-methyl-1-methylcarbamoyl-but-(Z)-ylidene]-amide [ No CAS ]
  • 17
  • [ 68-95-1 ]
  • [ 16395-58-7 ]
YieldReaction ConditionsOperation in experiment
79% To a solution of compound 1 (3.18 mmol, 500 mg) in dichloromethane was slowly added a solution of dicyclohexylcarbodiimide (6.37 mmol, 656 mg) in dichloromethane at 10-15 C (duration 5.0 min) and the mixture was stirred at room temperature for 1 h. To this, ammonium bicarbonate (3.18 mmol, 305 mg) was added and the mixture was stirred for 1 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was filtered and the residue was washed with dichloromethane. The filtrates were collected, combined, and concentrated under vacuum. The resulting gummy mass was suspended in tetrahydrofuran under stirring and diisopropyl ether was slowly added dropwise over 15 min. The mixture was then cooled to 0 C and allowed to stand at this temperature for 1 h. The resulting crystalline white solid was filtered, washed with diisopropyl ether, and dried under vacuum to afford the crude product 2. This was then purified by column chromatography to obtain (S)-1-acetylpyrrolidine-2-carboxamide 2. White solid (392 mg, 79%), mp 115 to 117 C, 1H NMR (300 MHz, CDCl3): δ 8.18 (s, 2H NH), 4.16 (t, 1H, J = 9.5 Hz, 6.1 Hz), 3.63 (t, 2H, J = 9.5 Hz, 6.0 Hz), 3.24 (q, 2H, J = 11.1 Hz, 7.1 Hz, 6.4 Hz), 2.48 (s, 3H), 2.19-2.26 (m, 2H); 13C NMR (300 MHz, CDCl3): δ 179.12, 175.54, 61.87, 50.07, 29.93, 24.32, 21.12; GC-MS m/z 156.20 (M+); Elemental Analysis: Calcd C7H12N2O2: C, 53.83; H, 7.74; N, 17.94; O, 20.49. Found C, 53.82; H, 7.76; N, 17.91; O, 20.48.
  • 18
  • [ 16395-58-7 ]
  • [ 124-63-0 ]
  • [ 1403959-03-4 ]
YieldReaction ConditionsOperation in experiment
84% With pyridine; for 14h; General procedure: General procedure for the synthesis of pyrrolidine sulfonamide organocatalysts 3a-c Compound 2 (4.43 mmol, 500 mg) was dissolved in a much smaller amount of pyridine; to this solution was added methanesulfonamide/p-toluenesulfonamide/p-nitrobenzenesulfonamide. This mixture was stirred for 1-2 h and then left overnight without stirring. After completion of the reaction, crushed ice was added to this mixture and the mixture was stirred again to obtain a solid crude product; if the mixture was slightly acidified, we did not obtain any product. This crude product was washed with dichloromethane and ice cold water. The product was further purified using column chromatography to obtain crystals of compounds 3a-c.
  • 19
  • [ 16395-58-7 ]
  • [ 98-59-9 ]
  • [ 1403959-04-5 ]
YieldReaction ConditionsOperation in experiment
87% With pyridine; for 14h; General procedure: General procedure for the synthesis of pyrrolidine sulfonamide organocatalysts 3a-c Compound 2 (4.43 mmol, 500 mg) was dissolved in a much smaller amount of pyridine; to this solution was added methanesulfonamide/p-toluenesulfonamide/p-nitrobenzenesulfonamide. This mixture was stirred for 1-2 h and then left overnight without stirring. After completion of the reaction, crushed ice was added to this mixture and the mixture was stirred again to obtain a solid crude product; if the mixture was slightly acidified, we did not obtain any product. This crude product was washed with dichloromethane and ice cold water. The product was further purified using column chromatography to obtain crystals of compounds 3a-c.
  • 20
  • [ 16395-58-7 ]
  • [ 98-74-8 ]
  • [ 1403959-05-6 ]
YieldReaction ConditionsOperation in experiment
88% With pyridine; for 14h; General procedure: General procedure for the synthesis of pyrrolidine sulfonamide organocatalysts 3a-c Compound 2 (4.43 mmol, 500 mg) was dissolved in a much smaller amount of pyridine; to this solution was added methanesulfonamide/p-toluenesulfonamide/p-nitrobenzenesulfonamide. This mixture was stirred for 1-2 h and then left overnight without stirring. After completion of the reaction, crushed ice was added to this mixture and the mixture was stirred again to obtain a solid crude product; if the mixture was slightly acidified, we did not obtain any product. This crude product was washed with dichloromethane and ice cold water. The product was further purified using column chromatography to obtain crystals of compounds 3a-c.
  • 21
  • [ 20354-32-9 ]
  • [ 16395-58-7 ]
  • C9H15N2O3PS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With pyridine; sulfur; at 20℃; for 3h; General procedure: To a solution of carboxamide 1a-f (1mmol) in dry pyridine (8mL) containing suspended elemental sulfur (1.5mmol), neat 2-chloro-1,3,2-oxathiaphospholane (2)21 (1.1mmol) was added dropwise. The reaction mixture was stirred at room temperature for 12h (for carboxamide derivatives) or 3h (for amino acid carboxamide derivatives). Then the solvent was removed under reduced pressure. To the residue, acetonitrile (10mL) was added and excess sulfur was filtered off. The solvent was evaporated under reduced pressure, the residue was dissolved in chloroform (2-3mL), and the sample was applied on a silica gel column (2.5×18cm). The column was eluted with a gradient of methanol in chloroform (0→1%). Appropriate fractions were combined and evaporated under reduced pressure. The yields of 3a-f, their chemical shift values (31P NMR), and FAB-MS data are presented in Table 1.
  • 22
  • [ 16395-58-7 ]
  • 2',2'-difluoro-2'-deoxycytidine-5'-O-[N-(α-N-acetylprolyl)]thiophosphoramidate [ No CAS ]
  • 23
  • [ 16395-58-7 ]
  • 2',2'-difluoro-2'-deoxycytidine-5'-O-[N-(α-N-acetyl prolyl)]phosphoramidate [ No CAS ]
  • 24
  • [ 147-85-3 ]
  • [ 16395-58-7 ]
  • 25
  • (S)-1-Acetyl-pyrrolidine-2-carbonyl chloride [ No CAS ]
  • [ 16395-58-7 ]
YieldReaction ConditionsOperation in experiment
97.2% With ammonium hydroxide; In dichloromethane; at 30℃; for 3h; 51.36 g of the compound (III) was reacted with 500 mL of a concentrated aqueous ammonia solution having a concentration of 25% at 30 C for 3 hours, and filtered to obtain 44.41 g of 1-acetyl-2-pyrrolidinecarboxamide (purity of 99.5%, yield: 97.2). %)
  • 26
  • [ 16395-58-7 ]
  • [ 7531-52-4 ]
YieldReaction ConditionsOperation in experiment
95.3% With hydrogenchloride; In water; at 103℃; for 2h; 44.41 g of 1-acetyl-2-pyrrolidinecarboxamide was added to 160 mL of 2N HCl.Raise the temperature to 103 C reflux reaction,During the reaction, the temperature of the system is kept at the micro-reflow state.Co-reacted for 2 hours,After completion of the reaction, the mixture was concentrated to a small volume until crystallization, pH was adjusted to 8, filtered, and dried to give the desired product, L-prolinamide, 31.05 g, yield 95.3%. Detection of D-type isomerismThe purity of the solution was 0.11%, and the purity was determined by high performance liquid chromatography HPLC to be 99.1%.
  • 27
  • [ 16395-58-7 ]
  • (S)-1-acetylpyrrolidine-2-carbonitrile [ No CAS ]
  • 28
  • [ 623-00-7 ]
  • [ 16395-58-7 ]
  • (R)-1-acetyl-N-(4-cyanophenyl)pyrrolidine-2-carboxamide [ No CAS ]
  • 1-acetyl-N-(4-cyanophenyl)pyrrolidine-2-carboxamide [ No CAS ]
  • 29
  • [ 108-24-7 ]
  • [ 16395-58-7 ]
  • [ 609-09-6 ]
  • diethyl α-acetoxy-α-[1-acetyl-L-prolylamino]malonate [ No CAS ]
  • 30
  • [ 16395-58-7 ]
  • diethyl α-(1-acetyl-L-prolylamino)-α-(1-methylindol-3-yl)malonate [ No CAS ]
  • 31
  • [ 16395-58-7 ]
  • 2-(1-acetyl-L-prolylamino)-2-(1-methylindol-3-yl)ethanoic acid [ No CAS ]
  • 32
  • [ 16395-58-7 ]
  • C14H20N2O6 [ No CAS ]
 

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