HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Azide → (Ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Azide | HCID 33557 | — |
| Reactant | (3S)-2,2-Dimethyl-3-(phenylmethoxy)pent-4-en-1-ol | HCID 10998568 | — |
| Reactant | (Ethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate | HCID 86628900 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | (Ethoxycarbonyloxy)ethyl (2R)-4-[(3-azidopropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate | HCID 86628901 | — |
Reaction Steps
Following the general procedure for the preparation of azides of Description 16, 11.0 g of a mixture of (ethoxycarbonyloxy)ethyl (2R)-4-[(3-chloropropyl)sulfonyloxy]-3,3-dimethyl-2-(phenylmethoxy)butanoate (32a) and (3R)-4,4-dimethyl-3-(phenylmethoxy)-3,4,5-trihydrofuran-2-one (1) dissolved in 100 mL of anhydrous dimethyl sulfoxide (DMSO) was reacted with 2.4 g (37 mmol) of sodium azide (NaN3). After work-up, the crude title compound (32b) was obtained and used in the next step without further purification. MS (ESI) m/z 524.07 (M+Na)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08168617B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-3ae1ebeb35974a5e9a32a1a70d9b92eb |
| Source note | uspto-grants-2012_05 |