HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1805361Generated: November 2, 2026
N,N'-Dimethylethylenediamine → (S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoate
https://huagongshe.com/reaction/1805361
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | N,N'-Dimethylethylenediamine | HCID 8070 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate | HCID 67229228 | — |
| Reactant | (S)-5'-fluoro-2,2-dimethylspiro[cyclopropane-1,3'-indolin]-2'-one | HCID 67230523 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (S)-methyl-3-(5'-fluoro-2,2-dimethyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)-5-(2-oxooxazolidin-3-yl)benzoate | HCID 58305358 | 80% |
Reaction Steps
A suspension of (R) and (S)-5′-fluoro-2,2-dimethylspiro[cyclopropane-1,3′-indolin]-2′-one (2 mmol) (prepared as in Example 100), methyl-3-bromo-5-(2-oxooxazolidin-3-yl)benzoate (682 mg, 2 mmol), CuI (76 mg, 0.4 mmol), potassium carbonate (545 mg, 4 mmol) and N,N′-dimethyl-ethane-1,2-diamine (86 uL, 0.8 mmol) in acetonitrile (15 mL) was stirred for 16 hours at 90° C. The precipitate was filtered off and washed with ethyl acetate. The filtrate was concentrated in vacuo to afford the title compound as white powder (480 mg, 80%) which was used for the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08354443B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-a45b143ce03e4bbd95ca59db818facf5 |
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| Source note | uspto-grants-2013_01 |
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