HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic Acid 4-nitrooxybutyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide | HCID 15908 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-(Nitrooxy)butan-1-ol | HCID 10011944 | — |
| Reactant | (2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic acid | HCID 67969342 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic Acid 4-nitrooxybutyl Ester | HCID 86703817 | 45.9% |
Reaction Steps
(2R,4R)-5-Biphenyl-4-yl-4-t-butoxycarbonylamino-2-hydroxypentanoic acid (30 mg, 78 μmol), HOBt (63 mg, 470 μmol), and EDCI (83 μL, 470 μmol) were dissolved into DCM. After stirring for 10 minutes, 4-nitrooxybutan-1-ol (84.1 mg, 623 μmol) was added. The resulting mixture was stirred at room temperature and the reaction monitored for completion (˜30 minutes). The mixture was stirred for an additional 2 hours and then left open to dry. The product was then purified (Interchim reverse phase chromatography column; 35-95% MeCN in water with 0.05% TFA) to yield the title compound (18 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09045443B2 |
| Source dataset | uspto-grants-2015_06 |
| ORD ID | ord-a3877d6a3b5f482bbdb2640bc72731fa |
| Source note | uspto-grants-2015_06 |