HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → (S)-2-Acetylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (S)-2-Amino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester | HCID 68839983 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (S)-2-Acetylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester | HCID 68842421 | — |
Reaction Steps
To a Solution of (S)-2-Amino-3-{3-Benzyloxy-4-[1,1,4-Trioxo-5-(2-Trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid tert-butyl ester (150 mg, 0.27 mmol) and triethylamine (0.57 mL, 0.41 mmol) in methylene chloride (10 mL) at 0° C. is added acetyl chloride (0.21 mL, 0.3 mmol) dropwise then the mixture is stirred at RT for 2 h. Water and 1N HCl is added until pH 4 and the mixture is extracted with methylene chloride. The organic phase is washed with brine and dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08084448B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-f3cec8b9fa604b489a9ec4737e214bcb |
| Source note | uspto-grants-2011_12 |