| Identification | Back Directory | [Name]
N,N-DIBENZYLGLYCINE ETHYL ESTER | [CAS]
77385-90-1 | [Synonyms]
Di-Bzl-Gly-OEt
Ethyl 2-(dibenzylamino)
Ethyl N,N-dibenzylglycinate
Ethyl (dibenzylamino)acetate
N,N-Dibenzyl-O-ethylglycinate
N,N-dibenzylglycine ethyl este
N,N-DIBENZYLGLYCINE ETHYL ESTER
N,N-DibenzylglycineEthylEster>
DIBENZYLAMINO-ACETIC ACID ETHYL ESTER
N,N-bis(phenylmethyl)Glycineethyl ester
N,N-DIBENZYLGLYCINE ETHYL ESTER USP/EP/BP
Glycine, N,N-bis(phenylmethyl)-, ethyl ester
N,N-Dibenzylglycine Ethyl Ester
2-[bis(phenylmethyl)amino]acetic acid ethyl ester | [Molecular Formula]
C18H21NO2 | [MDL Number]
MFCD00796343 | [MOL File]
77385-90-1.mol | [Molecular Weight]
283.365 |
| Chemical Properties | Back Directory | [Melting point ]
56 °C | [Boiling point ]
376℃ | [density ]
1.091 | [Fp ]
123℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
powder to crystal | [pka]
5.47±0.50(Predicted) | [color ]
White to Almost white | [InChI]
InChI=1S/C18H21NO2/c1-2-21-18(20)15-19(13-16-9-5-3-6-10-16)14-17-11-7-4-8-12-17/h3-12H,2,13-15H2,1H3 | [InChIKey]
AFMDCFOWHWNQBP-UHFFFAOYSA-N | [SMILES]
C(OCC)(=O)CN(CC1=CC=CC=C1)CC1=CC=CC=C1 |
| Hazard Information | Back Directory | [Chemical Properties]
White to almost white crystalline powder | [Synthesis]
GENERAL STEPS: A solution of dibenzylamine (0.3 mmol, dissolved in 4.0 mL of ether) was added to a solution of water (1.0 mL) containing Ru(II)-hm-pheox 3 (0.0075 mmol, 2.5 mol%), followed by the addition of ethyl diazidoacetate (0.3 mmol, 1.0 equiv). The two-phase reaction mixture was stirred at room temperature until the reaction was complete. At the end of the reaction, the ether layer was separated and removed by decantation, and the catalyst in the aqueous phase was washed three times with ether (3 x 5.0 mL). The combined ether phases contained the ethyl 2-(dibenzylamino)acetate product, which was dried over anhydrous Na2SO4 and concentrated under reduced pressure. In most cases, the purity of the product is sufficient and no further purification is required. The aqueous phase containing the catalyst can be recovered for reuse. For purification of the 2-piperazinone product, silica gel column chromatography was used, using only methanol as eluent. | [References]
[1] Tetrahedron Letters, 2017, vol. 58, # 51, p. 4750 - 4754
[2] Asian Journal of Chemistry, 2017, vol. 29, # 2, p. 349 - 352
[3] Tetrahedron Letters, 2014, vol. 55, # 40, p. 5417 - 5419
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 22, p. 5351 - 5354
[5] Tetrahedron Letters, 2009, vol. 50, # 31, p. 4467 - 4469 |
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