HuagongsheHuagongshe Chemistry Print Report · For research reference only
Heptanoic Acid → HCID 54165626, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Heptanoic Acid | HCID 8094 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (S)-methyl 2-amino-3-hydroxypropanoate | HCID 2723731 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | HCID 54165626 | HCID 54165626 | 79.5% |
Reaction Steps
To a solution of heptanoic acid (0.46 ml, 3.2 mmol) and H-Ser-OCH3 (0.5 g, 3.2 mmol) in CH2Cl2 (15 ml) were added HBTU (1.83 g, 4.8 mmol), HOBt (0.74 g, 4.8 mmol) and lastly diisopropylethylamine (2.8 ml, 16 mmol). Reaction was stirred overnight at room temperature. The resulting mixture was subjected to flash column chromatography (hexane/EtOAc, 1:2) yielding (S)—N-heptanoyl-serine methyl ester (588.6 mg, 79%) as yellowish oil. 1H NMR: δ=6.47 (b, 1H, NH), 4.69 (m, 1H, 2-H), 3.94 (m, 2H, 3-H), 3.79 (s, 3H, 1-OCH3), 2.27 (t, 3J=7.6 Hz, 2H, 2′-H), 1.63 (m, 2H, HHep), 1.29 (m, 6H, HHep), 0.88 (m, 3H, 7′-CH3) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07642369B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-d16d7970c13a4ded89ba5cfe90927ede |
| Source note | uspto-grants-2010_01 |