HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Isobutyl chloroformate | HCID 62365 | — |
| Reactant | (2S)-2-Amino-N-benzyl-3-methylbutanamide | HCID 11063601 | — |
| Reactant | 1-(2-adamantan-1-yl-2-oxoethyl) L-proline | HCID 54229701 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide | HCID 67634856 | 71.6% |
Reaction Steps
Using the procedure described in Example 3, a solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (109.1 mg, 0.37 mmol, 1.0 eq), triethylamine (156 uL, 1.12 mmol, 3.0 eq), and THF (1.5 mL), was treated with isobutyl chloroformate (53 uL, 0.41 mL, 1.1 eq), then with L-valine benzylamide (117.5 mg, 570 umol, 1.5 eq). Workup as before provided 127 mg (71%) of L-valine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide as a white foam.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05686424 |
| Source dataset | uspto-grants-1997_11 |
| ORD ID | ord-e5cd1097e4f44fa2a3dfc1165ce7f1b9 |
| Source note | uspto-grants-1997_11 |