HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 20429Generated: October 26, 2026
Cesium carbonate → (2R,5R)-5-{(1S,2S)-2-Acetylamino-3-[3-(2,2-difluoroethoxy)-phenyl]-1-hydroxypropyl}-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester
https://huagongshe.com/reaction/20429
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromo-1,1-difluoroethane | HCID 136186 | — |
| Reactant | (2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester | HCID 68562669 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (2R,5R)-5-{(1S,2S)-2-Acetylamino-3-[3-(2,2-difluoroethoxy)-phenyl]-1-hydroxypropyl}-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester | HCID 58972247 | — |
Reaction Steps
Dissolve (2R,5R)-5-[(1S,2S)-2-acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester (204 mg) and 2,2-difluoro-1-bromoethane (0.065 mL) and cesium carbonate (391 mg) in N,N-dimethylformamide (5 mL) and heat to 60° C. for 18 hours. Dilute with ethyl acetate, wash with saturated aqueous sodium chloride, dry and purify (silica gel chromatography, eluting with 1:1 ethyl acetate:dichloromethane), to give the desired compound (223 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07745438B2 |
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| Source dataset | uspto-grants-2010_06 |
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| ORD ID | ord-50f5559b755c41c4bb23b87a638117e2 |
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| Source note | uspto-grants-2010_06 |
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