HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 20405Generated: October 25, 2026
Ethyl Acetate → {(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester
https://huagongshe.com/reaction/20405
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N-Iodosuccinimide | HCID 120273 | — |
| Reactant | (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol | HCID 11065873 | — |
| Reactant | 1-(Ethenyloxy)-2,2-dimethylpropane | HCID 14897351 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | {(S)-2-benzyloxy-1-[1-(2,2-dimethylpropoxy)-2-iodoethoxymethyl]-ethyl}-carbamic acid tert-butyl ester | HCID 68561131 | 84.2% |
Reaction Steps
Add N-iodosuccinimide (14.19 g, 74.63 mmol) to ((R)-2-benzyloxy-1-hydroxymethylethyl)-carbamic acid tert-butyl ester (15.00 g, 53.30 mmol) and 2,2-dimethyl-1-vinyloxypropane (9.13 g, 79.96 mmol) in acetonitrile (267 mL) at room temperature. Heat to 60° C. under nitrogen for 2 hours. Cool to room temperature and dilute with ethyl acetate. Wash with water and saturated aqueous sodium chloride. Dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the desired compound as an oil (23.4 g 84.2%).
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-bffe4dffcbdc41dca34b21a93476b393 |
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| Source note | uspto-grants-2010_06 |
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