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Chemical Structure| 2788-84-3 Chemical Structure| 2788-84-3

Structure of 2788-84-3

Chemical Structure| 2788-84-3

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Product Details of [ 2788-84-3 ]

CAS No. :2788-84-3
Formula : C4H9NO3
M.W : 119.12
SMILES Code : N[C@@H](CO)C(OC)=O
MDL No. :MFCD07783983

Safety of [ 2788-84-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 2788-84-3 ]

* 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 [ 2788-84-3 ]

[ 2788-84-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 66065-85-8 ]
  • [ 2788-84-3 ]
  • [ 88050-18-4 ]
  • 2
  • [ 2788-84-3 ]
  • [ 86688-96-2 ]
  • [ 132081-32-4 ]
  • 3
  • [ 39067-29-3 ]
  • [ 2788-84-3 ]
  • (S)-3-Hydroxy-2-[(2-pyridin-3-yl-thiazole-4-carbonyl)-amino]-propionic acid methyl ester [ No CAS ]
  • 4
  • [ 2788-84-3 ]
  • [ 40350-83-2 ]
  • tert-butyl (2S,4R)-4-benzyloxy-2-[(2-hydroxy-1-methoxycarbonylethyl)carbamoyl]pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 48h; Benzyloxy-proline 1b (5.20 g, 16.2 mmol), L-serine methyl ester 8 (2.77 g, 17.8 mmol) and HOBt (3.72 g, 24.3 mmol) were added to flask with stir bar and dissolved in DCM (150 mL). DIPEA (6.93 mL, 40.5 mmol) was then added by syringe, followed by EDC-HCl (4.65 g, 24.3 mmol). The reaction was stirred at room temperature for 48 h, then the reaction was washed with water (~125 mL), 1M HCl (~125 mL), then saturated sodium bicarbonate (~125 mL). The organic portion was dried with sodium sulfate, filtered, and concentrated to a white foam. The crude compound was dissolved in DCM (~10 mL) and purified by flash chromatography (100 g SiO2 cartridge; 0-10% MeOH/DCM gradient) to yield the title compound (6.45 g, 94%) as a white foam. [alpha]D20 +75 (0.010, DCM); IR (thin film): 3421.0, 2976.9, 1746.3, 1668.8, 1525.8, 1392.9, 1206.3, 1160.6, 1068.7, 909.5 cm-1; 1H NMR (400 MHz, CDCl3) delta ppm 1.47 (s, 9H) 2.25 (s, 1H) 2.29 (d, J=5.9 Hz, 1H) 3.24-3.49 (m, 1H) 3.57 (br, 1H) 3.67 (br, 1H) 3.78 (s, 2H) 3.85 (br, 2H) 4.12 (br, 2H) 4.18-4.28 (m, 1H) 4.32 (t, J=7.4 Hz, 1H) 4.45-4.57 (m, 2H) 4.62 (br, 1H) 6.95-7.11 (m, 1H) 7.21-7.40 (m, 5H); 13C NMR (75 MHz, CDCl3) delta=21.3, 28.53, 35.1, 52.9, 55.6, 59.6, 62.3, 70.6, 71.3, 81.16, 127.83, 127.92, 128.1, 128.6, 128.7, 137.8, 155.4, 171.0, 171.4, 172.1; HRMS (ESI+) calcd for C21H30N2O7 [M+H] 423.2125, found 423.2120.
  • 5
  • [ 2788-84-3 ]
  • [ 32926-43-5 ]
  • methyl 2-{(S)-2-(tert-butoxycarbonylamino)-3-(1-triphenylmethyl-1H-imidazol-4-yl)propanamido}-3-hydroxypropanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 15 - 30℃; for 3h;Large scale; 2200 g (4.42 mol, 1.0 eq) of <strong>[32926-43-5](S)-2-(tert-butoxycarbonylamino)-3-(1-trityl-1H-imidazol-4-yl)propanoic acid</strong> was dissolved in dimethylformamide In 15L,1042 g of pyridine (13.17 mol, 3.0 eq) was added.Add serine methyl ester hydrochloride 753 g (4.84 mol, 1.1 eq);EDCI 1011g (5.30 mol, 1.2 eq) was added in portions.Control the internal temperature is less than 15 °C, plus,The reaction was carried out at 20-30 ° C for 3 h. Pour the reaction solution into ice water 45L.A large amount of solid precipitated. Filtration, filter cake dissolved in EA / THF = 5 / 1 15L,Wash once with 1N HCl 5L, wash once with 5L of saturated saline solution.Yuanming powder is dry. Filtration, concentration of the organic phase under reduced pressure to a large amount of solids.Add 5L of petroleum ether to beat and filter.Drying to obtain 2500 g of methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-(1-tritylmethyl-1H-imidazol-4-yl)propanamide)-3-hydroxypropanoate, The yield was 95percent.
 

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