HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → (3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Tetrabutylammonium Fluoride Trihydrate | HCID 11726816 | — |
| Reactant | Acetonitrile--water (1/1) | HCID 18373917 | — |
| Reactant | (3S*,4R*)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 131728362 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | HCID 59512299 | — |
Reaction Steps
The title compound is prepared in a similar manner as described for Example 9/reaction step H, from (3S*,4R*)-3-(tert-butyl-dimethyl-silanyloxymethyl)-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (25.0 g, 41.1 mmol) and tetrabutylammonium fluoride trihydrate (19.4 g, 61.6 mmol) in THF (150 mL) as a colorless oil. MS: 495.2 [M+H]+; tR (HPLC, C18 column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/1.5 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 4.84 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07807709B2 |
| Source dataset | uspto-grants-2010_10 |
| ORD ID | ord-673a6965d32c432096f40f8fabbd137e |
| Source note | uspto-grants-2010_10 |