HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2204975Generated: October 31, 2026
Dodecanoyl chloride → (5R,9R)-tert-butyl 9-dodecanamido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate
https://huagongshe.com/reaction/2204975
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dodecanoyl chloride | HCID 8166 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | (5R,9R)-tert-butyl 9-azido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate | HCID 86678275 | — |
| Catalyst | Palladium hydroxide | HCID 9942167 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | (5R,9R)-tert-butyl 9-dodecanamido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate | HCID 71294491 | — |
Reaction Steps
A mixture of (5R,9R)-tert-butyl 9-azido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate (1.0 eq), Pd(OH)2 (0.5 eq), dodecanoyl chloride (2.4 eq), and DIEA (4.8 eq) in EtOAc (0.01 M) was stirred under H2 (1 atm) at 25° C. overnight. The reaction was filtered and washed with DCM. The filtrate was concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% EtOAc/Hex to give (5R,9R)-tert-butyl 9-dodecanamido-1-(9H-fluoren-9-yl)-3-oxo-2,11-dioxa-7-thia-4-azaheptacosane-5-carboxylate as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365506B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-6df4dad04c0942369aa2ff52aecad4df |
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| Source note | uspto-grants-2016_06 |
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