HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → {(2R,3S)-4-(3,5-difluoro-phenyl)-3-[3-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-5-(1-hydroxy-ethyl)-benzoylamino]-2-hydroxy-butyl}-(3-methoxy-benzyl)-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | [(2R,3S)-3-[3-acetyl-5-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-benzoylamino]-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester | HCID 57529282 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | {(2R,3S)-4-(3,5-difluoro-phenyl)-3-[3-(1,1-dioxo-1lambda6-[1,2]thiazinan-2-yl)-5-(1-hydroxy-ethyl)-benzoylamino]-2-hydroxy-butyl}-(3-methoxy-benzyl)-carbamic acid tert-butyl ester | HCID 57529323 | — |
Reaction Steps
[(2R,3S)-3-[3-Acetyl-5-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-benzoylamino]-4-(3,5-difluoro-phenyl)-2-hydroxy-butyl]-(3-methoxy-benzyl)-carbamic acid tert-butyl ester (16 mg, 0.022 mmol) was dissolved in MeOH (0.2 mL) and sodium borohydride (1.13 mg, 0.03 mmol) was added. The reaction mixture was stirred at room temperature for 2 h. The mixture was concentrated and partitioned between ethyl acetate and H2O. The organic layer was separated and concentrated to give the title compound which was used in the next step without further purification: HPLC retention time: 2.073 min (method A). MS (ESI) (M+H)+ 718.30.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07476764B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-d129e75359fd4363ae549803a9ac05b9 |
| Source note | uspto-grants-2009_01 |