HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → tert-butyl N-[3-[1-(5-benzyl-3-methyl-4-oxo-[1,2]oxazolo[5,4-d]pyrimidin-6-yl)propyl-(4-methylbenzoyl)amino]propyl]carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Methylbenzoyl Chloride | HCID 13405 | — |
| Reactant | tert-butyl N-[3-[1-(5-benzyl-3-methyl-4-oxo-[1,2]oxazolo[5,4-d]pyrimidin-6-yl)propylamino]propyl]carbamate | HCID 57587937 | — |
| Solvent | Chloroform | HCID 6212 | — |
| Product | tert-butyl N-[3-[1-(5-benzyl-3-methyl-4-oxo-[1,2]oxazolo[5,4-d]pyrimidin-6-yl)propyl-(4-methylbenzoyl)amino]propyl]carbamate | HCID 68827326 | 95.1% |
Reaction Steps
A solution of the compound of Example 1 Step 5 (50 mg, 0.11 mmol) in CHCl3 (10 mL) was treated with 4-toluoyl chloride (16.9 mg, 0.11 mmol) followed by Et3N (11.1 mg, 0.11 mmol). The resulting mixture was stirred at room temperature for 18 h, then concentrated under vacuum. The crude product was purified by preparative reverse-phase HPLC on a YMC S5 ODS 30×100 mm column to afford the desired product as a yellow glass (60 mg, 95%); LC/MS 100% at 4.32 min (ESI): 574 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07022850B2 |
| Source dataset | uspto-grants-2006_04 |
| ORD ID | ord-7b0486ecebed4f1d9fb79000a09b1acd |
| Source note | uspto-grants-2006_04 |