HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | Ureidovaline | HCID 9818282 | — |
| Reactant | 1,3-Thiazol-5-ylmethyl N-((1S,2S,4S)-4-amino-1-benzyl-2-hydroxy-5-phenylpentyl)carbamate | HCID 11101978 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2S,3S,5S)-2-amino-5-(N-((5-thiazolyl)methoxycarbonyl) amino)-1,6-diphenyl-3-hydroxyhexane | HCID 10812314 | 126.3% |
Reaction Steps
A solution of 70 mg (0.223 mmol) of N-((N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine, 79 mg (0.186 mmol) of (2S,3S,5S)-5-amino-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-1,6-diphenyl-3-hydroxyhexane, 30 mg (0.223 mmol) of 1-hydroxybenzotriazole hydrate, and 51 mg (0.266 mmol) of N-ethyl-N'-dimethylaminopropyl carbodiimide in 2 ml of THF was stirred at ambient temperature for 16 h. The resulting solution was concentrated in vacuo, and the residue was purified by silica gel chromatography using 97:3 CH2Cl2 :CH3OH to provide 100 mg (74%) of the desired compound (Rf 0.4, 95:5 CH2Cl2 :CH3OH) as a solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05886036 |
| Source dataset | uspto-grants-1999_03 |
| ORD ID | ord-14dae71ee42f4735aae1ccc7d9144d9b |
| Source note | uspto-grants-1999_03 |