Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Dichlorophosphoryloxynaphthalene | HCID 575631 | — |
| Reactant | 39825-33-7 | HCID 13089459 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66779574 | HCID 66779574 | 92.5% |
Reaction Steps
(S)-isopropyl 2-aminopropanoate hydrochloride (Oakwood, 1.28 g, 7.64 mmol) and naphthalen-1-yl phosphorodichloridate (2 g, 7.66 mmol) was suspended in anhydrous DCM (35 mL). The reaction was cooled to −78° C. Triethylamine (1.55 g, 2.13 mL, 15.3 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, then warmed up to room temperature and stirred for 5 h. The solvent was removed, and the residue was washed with dry ethyl ether and filtered. The filtrate was concentrated to give crude (2S)-isopropyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate as a light yellow oil (2.5 g, 92%) and used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09108999B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-37273bec7e8142938fa0e975d45921d9 |
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| Source note | uspto-grants-2015_08 |
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