HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloromethyl chloroformate → (1S,3S)-1-((1S)-1-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-2-phenylethyl)-3-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-4-(4-pyridin-2-ylphenyl)butyl chloromethyl carbonate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloromethyl chloroformate | HCID 62754 | — |
| Reactant | A-792611 | HCID 11274374 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (1S,3S)-1-((1S)-1-{[(2S)-2-(3-benzyl-2-oxoimidazolidin-1-yl)-3,3-dimethylbutanoyl]amino}-2-phenylethyl)-3-{[N-(methoxycarbonyl)-3-methyl-L-valyl]amino}-4-(4-pyridin-2-ylphenyl)butyl chloromethyl carbonate | HCID 67407717 | 84.5% |
Reaction Steps
To a solution of the product from Example 111 (0.050 g, 0.062 mmol) in pyridine (0.60 mL) at room temperature was added chloromethyl chloroformate (0.007 mL, 0.079 mmol), and the mixture was stirred for 30 minutes. Additional chloromethyl chloroformate (0.007 mL) was added and the reaction was stirred for 30 minutes. The reaction was diluted with ethyl acetate and washed with dilute NaHCO3 and brine. The organic was dried over MgSO4, filtered and evaporated to give the title compound (0.047 g, 84% yield), which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07834043B2 |
| Source dataset | uspto-grants-2010_11 |
| ORD ID | ord-3217ef6c38684e0494b14fe2cbc016d9 |
| Source note | uspto-grants-2010_11 |