Structure of 7622-23-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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| CAS No. : | 7622-23-3 |
| Formula : | C13H18O3 |
| M.W : | 222.28 |
| SMILES Code : | O=C(OC(C)(C)C)[C@@H](O)CC1=CC=CC=C1 |
| MDL No. : | MFCD11042373 |
| InChI Key : | GMYNKCIZSNJVEE-NSHDSACASA-N |
| Pubchem ID : | 11276097 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H302 |
| Precautionary Statements: | P280-P305+P351+P338 |
* 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.

[ 7622-23-3 ]

[ 7622-23-3 ]
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[ 552-16-9 ]
[ 7622-23-3 ]
[ 7622-23-3 ]
[ 7622-23-3 ]
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[ 7622-23-3 ]
[ 7622-23-3 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 85.5% | With silver(l) oxide; In tetrahydrofuran; at 0 - 20℃; for 48h; | General procedure: To a stirred solution of tert-butyl ethyl(2-oxo-2-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenylamino)ethyl)carbamate (4a) (1.0 g, 2.36 mmol) in THF (10 mL) was added <strong>[7622-23-3](S)-tert-butyl 2-hydroxy-3-phenylpropanoate</strong> (7) (0.629 g, 2.83 mmol) followed by Ag2O (1.09 g, 4.728 mmol) at 0 oC and the reaction mixture was allowed to stirred at RT for 48 h. The reaction mixture was filtered over celite and washed with THF. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane-EtOAc 7/3) to afford compound 8a (1.3 g, 85.5%) as a brown semi solid (mixture of rotamers); [alpha] D25 = -7.11 (c 0.5, CHCl3); SFC: Chiralpak IC(4.6x250)mm5mu, CO2-0.5 % DEA in MeOH,60:40 flow rate = 4 g/min, tR = 6.81 min; IR (KBr): 3466, 3307, 2977, 1745, 1694 cm-1; 1H NMR (400 MHz, DMSO-d6, VT NMR, 90 C): delta 11.05 (br.s, 1H, D2O exchangeable), 10.82 (brs, 1H, D2O exchangeable), 8.44 - 8.39 (m, 2H), 7.99 (dd, J = 7.6, 1.2 Hz, 1H),7.78 (d, J = 8 Hz, 1H) 7.70 - 7.65 (m, 1H), 7.57 - 7.53 (m, 1H), 7.30 - 7.227 (m, 4H), 7.22-7.19 (m, 2H), 5.34 (t, J = 6.8 Hz, 1H), 3.91 (s, 2H), 3.30 (q, J = 6.8 Hz, 2H), 3.22 (d, J = 6.4 Hz, 2H), 1.32 (s, 18H), 1.06 (t, J = 7.2 Hz, 3H); HRMS (ESI): calcd for C36H44N3O8 [M + H]+ 646.3123; found 646.3113. |
[ 7622-23-3 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1.35 g | With silver(l) oxide; In tetrahydrofuran; at 0 - 20℃; for 48h; | General procedure: To a stirred solution of tert-butyl methyl(2-oxo-2-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenylamino)ethyl)carbamate (4b) (1.1 g, 2.68 mmol) in THF (10 mL) was added <strong>[7622-23-3](S)-tert-butyl 2-hydroxy-3-phenylpropanoate</strong> (7) (0.71g, 3.22 mmol) followed by Ag2O (1.24 g, 5.36 mmol) at 0 oC and reaction mixture was allowed to rt, stirred for 48 h. The reaction mixture was filtered over celite and washed with THF. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column (Hexane-EtOAc 7/3) to afford compound 8b (1.35 g, 80%) as a brown semi solid (mixture of rotamers); [alpha] D25 = -6.51 (c 0.5, CHCl3); SFC: Chiralpak IC(4.6x250)mm5mu, CO2-0.5 % DEA in MeOH,60:40 flow rate = 3 g/min, tR = 6.18 min; IR (KBr): 3271, 2978, 1748, 1694, 1253 cm-1; 1H NMR (400 MHz, DMSO-d6, VT NMR, 90 C): delta 11.1 (br.s, 1H, D2O exchangeable), 10.80 (br.s, 1H, D2O exchangeable), 8.43 (d, J = 8.4 Hz, 1H), 8.37 (d, J = 8.4 Hz, 1H), 7.99 (dd, J = 7.6, 1.2 Hz, 1H), 7.78 (dd, J = 8.0, 1.6 Hz, 1H), 7.70 - 7.65 (m, 1H), 7.58 - 7.53 (m, 1H), 7.30 - 7.25 (m, 4H), 7.23 - 7.18 (m, 2H), 5.34 (t, J = 6.0 Hz, 1H), 3.93 (s, 2H), 3.22 (d, J = 6.4 Hz, 2H), 2.89 (s, 3H), 1.33 (s, 18H); HRMS (ESI): calcd for C35H42N3O8 [M + H]+ 632.2966; found 632.2957. |