HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dichloroethane → 4-[2-(1-Benzyl-imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dichloroethane | HCID 11 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-[2-(N-Benzylimidazol-4-yl)ethyloxy]benzoic acid | HCID 15850757 | — |
| Reactant | (S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochloride | HCID 22853534 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-[2-(1-Benzyl-imidazol-4-yl)ethyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine tert-butyl ester | HCID 15850721 | — |
Reaction Steps
A stirred mixture of 3-6 (147 mg, 0.46 mmol), HOBT (94 mg, 0.61 mmol), 2-1 (154 mg, 0.46 mmol), NMM (100 μL, 0.91 mmol), and DMF (1.2 mL) at 0° C. was treated with EDC (118 mg, 0.61 mmol) followed by removal of the cooling bath. The reaction pH was adjusted to 8 by addition of more NMM. After 20 h the reaction mixture was concentrated and the residue purified by to a flash chromatography column (silica, 9/0.5/0.5 CH2Cl2 /CH3OH/AcOH) to give 3-7 as a yellow solid after azeotropic removal of residual AcOH with toluene. Rf 0.48 (silica, 9/0.5/0.5 CH2Cl2 /CH3OH/AcOH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05929120 |
| Source dataset | uspto-grants-1999_07 |
| ORD ID | ord-598bdbbe2fe84fe1a0167b6bc7f97547 |
| Source note | uspto-grants-1999_07 |