HuagongsheHuagongshe Chemistry Print Report · For research reference only
Carbon dioxide methanol → tert-Butyl (4aS,7aS)-7a-(2-fluoro-5-(5-fluoropicolinamido)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-ylcarbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Carbon dioxide methanol | HCID 21973728 | — |
| Reactant | tert-butyl 7a-(5-(5-fluoropicolinamido)-2-fluorophenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-ylcarbamate | HCID 66861447 | — |
| Product | tert-Butyl (4aS,7aS)-7a-(2-fluoro-5-(5-fluoropicolinamido)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-ylcarbamate | HCID 58102210 | 41% |
Reaction Steps
Racemic tert-butyl (4aSR,7aSR)-7a-(2-fluoro-5-(5-fluoropicolinamido)phenyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-ylcarbamate (0.226 g, 0.460 mmol) is purified by chiral HPLC: 2.1×25 cm Chiralcel OD-H, 5 micron column, 30% methanol/CO2, flow rate: 70 mL/min, UV: 230 nm. The second eluting isomer is isolated to provide the enantiomerically enriched title compound (0.092 g, 41%). ES/MS (m/e): 491 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08278441B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-77e3caacc4514c23ace08ee8fd960a2b |
| Source note | uspto-grants-2012_10 |