N-(Diphenylmethylene)glycerine tert-butyl ester CAS 81477-94-3
N-(Diphenylmethylene)glycerine tert-butyl ester Basic information
| Product Name: | N-(Diphenylmethylene)glycerine tert-butyl ester |
| Synonyms: | N-(Diphenylmethylene)glycine tert-butyl ester;ETHYL (DIPHENYLMETHYLENAMINO)ACETATE;BP-GLY-OTBU SCHIFF BASE;AURORA KA-6707;TERT-BUTYL (DIPHENYLMETHYLENEAMINO)ACETATE;T-BUTYL-N-(DIPHENYLMETHYLENE) GLYCINATE;N-(DIPHENYLMETHYLENE)GLYCINE, T-BUTYL ESTER;tert-butyl 2-((diphenylmethyle |
| CAS: | 81477-94-3 |
| MF: | C19H21NO2 |
| MW: | 295.38 |
| EINECS: | 1533716-785-6 |
| Product Categories: | Amino Acids 13C, 2H, 15N;Glycine Equivalents;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Amino Acids & Derivatives |
| Mol File: | 81477-94-3.mol |
N-(Diphenylmethylene)glycerine tert-butyl ester Chemical Properties
| Melting point | 51-53 °C(lit.) |
| Boiling point | 377.5±34.0 °C(Predicted) |
| density | 1.00±0.1 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | crystal |
| pka | 2.31±0.50(Predicted) |
| color | white |
| Water Solubility | Insoluble in water. |
| Stability: | Moisture Sensitive |
| InChI | InChI=1S/C19H21NO2/c1-19(2,3)22-17(21)14-20-18(15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-13H,14H2,1-3H3 |
| InChIKey | YSHDPXQDVKNPKA-UHFFFAOYSA-N |
| SMILES | C(OC(C)(C)C)(=O)C/N=C(/C1=CC=CC=C1)\C1=CC=CC=C1 |
Safety Information
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25 |
| WGK Germany | 3 |
| F | 10-21 |
| TSCA | No |
| HS Code | 29163990 |
| Chemical Properties | White Solid |
| Uses | suzuki reaction |
| Uses | N-(Diphenylmethylene)glycine tert-butyl ester is a useful dye for biological research purposes. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields. |
| Synthesis | 1013-88-3 5292-43-3 81477-94-3 The intermediate was synthesized by a general procedure based on US2010/0189644 and the disclosure of O'Donnell et al. The procedure was carried out as follows: benzophenone imine (8.6 g, 47.5 mmol), tert-butyl bromoacetate (9.3 g, 47.5 mmol), and acetonitrile (40 mL) were added to a round-bottomed flask equipped with a stirrer. After heating the reaction mixture to 70 °C, N,N-diisopropylethylamine (DIPEA, 8.3 mL, 47.5 mmol) was slowly added. A reflux condenser was installed and the reaction was maintained at 70 °C for 16 hours. The reaction progress was monitored by HPLC and TLC and after confirming the complete conversion of the reactants, the reaction mixture was cooled to room temperature. A 5:3 mixture of water/formic acid (1 mL) was added, followed by concentration of the reaction mixture under reduced pressure. The resulting solid was washed sequentially with 3:1 cold solution of water/ethanol (2 x 60 mL) and 1:1 cold solution of water/ethanol (30 mL). The solid was dried under high vacuum to afford tert-butyl N-diphenylmethylene-glycinate (14.9 g, 47.0 mmol, 99% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, CDCl3) and mass spectrometry (LC/MS): 1H NMR δ 7.66 (2H, m), 7.47 (3H, m), 7.41 (1H, t, J=8 Hz), 7.34 (1H, t, J=8 Hz), 7.20 (2H, m), 4.13 (2H, s), 1.48 (9H, s); MS (LC/MS) m/z measured value 195.93, theoretical value 296.16 [M+H]+. |
| References | [1] Patent: WO2016/15159, 2016, A1. Location in patent: Page/Page column 56 [2] Patent: US9458192, 2016, B1. Location in patent: Page/Page column 44-45 [3] European Journal of Organic Chemistry, 2005, # 2, p. 317 - 325 [4] Chemical Communications, 2009, # 2, p. 168 - 170 [5] Patent: US2010/189644, 2010, A1. Location in patent: Page/Page column 23 |
N-(Diphenylmethylene)glycerine tert-butyl ester Preparation Products And Raw materials
| Raw materials | Diethyl ether-->Dichloromethane-->Magnesium sulfate-->Hexane-->Ammonium chloride-->Benzophenone imine-->Glycine tert butyl ester hydrochloride-->Benzophenone-->tert-Butyl glycinate-->tert-Butyl bromoacetate |
| Preparation Products | L-Tyrosine, O-(phenylmethyl)-, 1,1-dimethylethyl ester-->H-Glu(OMe)-OtBu-->D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid |
