HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Hydroxybenzotriazole → HCID 59784110, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Boc-L-Valine | HCID 83693 | — |
| Reactant | Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 2733084 | — |
| Reactant | HCID 59440290 | HCID 59440290 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 59784110 | HCID 59784110 | 64% |
Reaction Steps
The deprotected piperazine 3 (16.20 g, 41.2 mmol) is coupled with BOC-L-valine (8.95 g, 41.2 mmol) using DIEA (36.0 mL, 0.21 mol), HBTU (17.19 g, 45.3 mmol) and HOBt (6.12 g, 45.3 mmol) in DMF (700 mL) under the same conditions as in step 1 above. Purification is carried out by flash chromatography on silica gel (CH2Cl2 as eluent initially, followed by 10% Et2O/CH2Cl2 to elute the desired product). The desired coupled product 4 is isolated as a white foam (15.51 g, 64% yield): 1H NMR δ (CDCl3) 6.99-7.64 (m, 9H), 5.99-6.34 (br m, 1H), 2.68-5.26 (br m, 11H), 1.51-2.15 (br m, 6H), 1.42 (s, 9H), 1.15 (s, 3H), 0.64-1.02 (br m, 5H); LCMS (APCl+) 594.2 (MH+), 537.9 (MH+-tBu), 493.7 (MH+-BOC, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07932255B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-eb9f8e8e05a4414e899a4b13f3f4887e |
| Source note | uspto-grants-2011_04 |