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Chemical Structure| 62860-12-2 Chemical Structure| 62860-12-2

Structure of D-Pyroaspartic Acid
CAS No.: 62860-12-2

Chemical Structure| 62860-12-2

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Product Details of [ 62860-12-2 ]

CAS No. :62860-12-2
Formula : C4H5NO3
M.W : 115.09
SMILES Code : O=C([C@@H](C1)NC1=O)O
English Name :(R)-4-Oxoazetidine-2-carboxylic acid
MDL No. :MFCD16036189
InChI Key :YSPMLLKKKHCTBN-UWTATZPHSA-N
Pubchem ID :10176125

Safety of [ 62860-12-2 ]

Application In Synthesis of [ 62860-12-2 ]

* 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 [ 62860-12-2 ]

[ 62860-12-2 ] Synthesis Path-Downstream   1~4

YieldReaction ConditionsOperation in experiment
1 (2R)-4oxoazetidine-2-carboxylic acid (2R)-4oxoazetidine-2-carboxylic acid A solution of benzyl (2R)-4-oxoazetidine-2-carboxylate (20.1 kg, 98.05 mol) in THF (201 L) was added to Pd/C (1.005 kg) in a 100 gallon hydrogenation reactor. The reaction mixture was stirred under hydrogen (24-26 psi) at 21-24° C. until thin layer chromatography (hexane/ethyl acetate, 1:1) showed disappearance of starting material (8 hours). The mixture was filtered to provide a solution of (2R)-4-oxoazetidine-2-carboxylic acid in THF. 1 H NMR (DMSO-d6) δ 8.28 (br, 1H), 4.03 (dd, J=5.9, 2.6 Hz), 3.19 (ddd, J=14.5, 5.8, 1.4 Hz), 2.83 (ddd, J=14.6, 2.6, 1.7 Hz).
  • 2
  • [ 62860-12-2 ]
  • [ 1313991-83-1 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; aniline; trifluoroacetic acid In dichloromethane 21 Example 21 Example 21 (3S,6S,10aS)-6-((S)-2-(methylamino)propanamido)-5-oxo-N-(3-((R)-4-oxoazetidine-2-carboxamido)benzyl)decahydropyrrolo[1,2-a]azocine-3-carboxamide: The title compound was prepared according to the steps and intermediates as described below. To a mixture of the aniline 1k (16 mg), (R)-4-oxo-2-azetidinecarboxylic acid (12 mg), EDC.HCl (20 mg), HOBt (14 mg), disoppropylethylamine (20 μl) in dichloromethane (1 mL) was stirred overnight at RT. After stirring for 10 min at 0° C., trifluoroacetic acid (0.3 mL) was added to the reaction mixture and stirred 10 min at rt. The reaction mixture was concentrated and the residue was purified using semi-prep HPLC (TFA modifier) to give a white solid as TFA salt. LCMS: m/e 513.3 (M+1).
  • 3
  • [ 62860-12-2 ]
  • [ 2222938-95-4 ]
  • [ 2983002-82-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (2R)-4-oxoazetidine-2-carboxylic acid; 4-(3,5-dimethylisoxazol-4-yl)-N1-((1r,4r)-4-methoxycyclohexyl)benzene-1,2-diamine With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 12h; Stage #2: With acetic acid at 80℃; for 20h; 5.1.4 General Procedure for synthesis of 8a-8q General procedure: To a stirred solution of carboxyl derivatives 7a-7g (0.6mmol) in 5mL of DMF, HATU (304.2mg, 0.8mmol), DIPEA (129.1mg, 1.0mmol) and 6a-6k (0.5mmol) were added sequentially, and the reaction was stirred at room temperature for 12h. After the reaction was completed, the reaction mixture was diluted with EtOAc (20mL). The organic layer was washed with brine, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. The crude product was put in 5mL acetic acid and heated at 80°C for 20h. After the reaction was completed, the reaction mixture was cooled to room temperature, concentrated under vacuum and diluted with EtOAc (20mL). The organic layer was washed with saturated NaHCO3 aqueous solution and brine, dried with anhydrous Na2SO4, filtered and concentrated under vacuum. The crude product was purified by flash chromatography to provide the desired product.
  • 4
  • [ 62860-12-2 ]
  • [ 2222938-95-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; 4.1.23. General procedure for the synthesis of 19a and 19b General procedure: To a stirred solution of (S) or (R)-4-oxoazetidine-2-carboxylic acid(1.1 equiv) in 5 DMF (5 mL), HATU (1.5 equiv), DIPEA (3 equiv), and17a (1 equiv) were added sequentially, and the reaction was stirred atroom temperature for 5 h. After the reaction was completed, the reactionmixture was diluted with EtOAc (50 mL). The organic layer was washedwith brine, dried with anhydrous Na2SO4, filtered, and concentratedunder vacuum to obtain the crude amide intermediates that can be usedin the next step without purification. Then the above amide intermediatesin acetic acid (5 mL) were heated at 80 for 12 h. After thereaction was completed, the reaction mixture was cooled to room temperature,concentrated under vacuum and diluted with EtOAc (20 mL).The organic layer was washed with saturated NaHCO3 aqueous solutionand brine, dried with anhydrous Na2SO4, filtered, and concentratedunder vacuum. The crude product was purified by flash chromatographyto provide the desired product in 40-60% yield.
 

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