HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzaldehyde → (R)-methyl 2-(benzylamino)-3-phenylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sulfuric acid magnesium salt (1:1) | HCID 24083 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | methyl (2R)-2-amino-3-phenylpropanoate;hydrochloride | HCID 11481330 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (R)-methyl 2-(benzylamino)-3-phenylpropanoate | HCID 13388971 | 72.6% |
Reaction Steps
Synthesized according to the general procedure as described in Example 1a using D-phenylalanine methyl ester hydrochloride (2 gm, 9.2 mmol), THF (25 mL), MgSO4 (1.87 gm, 15.6 mmol), benzaldehyde (1.88 mL, 18.5 mmol), Et3N (1.28 mL, 9.2 mmol), sodium borohydride (699 mg, 18.5 mmol), and methanol (30 mL) to give 11g (1.8 gm, 72%) in FIG. 2. 1H NMR (500 MHz, CD3OD): δ 2.96 (2H, d, J=6.59 Hz), 3.53 (1H, t, J=7.08 Hz), 3.6 (3H, s), 3.63 (1H, d, J=12.93 Hz), 3.77 (1H, d, J=12.93 Hz), 7.13-7.18 (2H, m), 7.19-7.32 (8H, m). ESI-MS: 292.2 (M+23).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08552208B2 |
| Source dataset | uspto-grants-2013_10 |
| ORD ID | ord-efc86669632a443691cde596162ae3c9 |
| Source note | uspto-grants-2013_10 |