Dichloromethane → (2S)-isobutyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate

HRID 408973

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:21])[C:14]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15].[P:22](Cl)(Cl)(=[O:34])[O:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1.C(Cl)[Cl:38]>>[Cl:38][C:25]1[CH:26]=[CH:27][C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]=1[O:23][P:22](=[N:12][C@@H:13]([CH3:21])[C:14]([O:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:15])=[O:34]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 137435562-methylpropyl (2S)-2-aminopropanoate

Product 1

HCID 66778743(2S)-isobutyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates, the tosylate salt of (S)-isobutyl 2-aminopropanoate (2.5 g), naphthalen-1-yl phosphorodichloridate (2.06 g), TEA (2.19 mL) and DCM (50 mL) were combined to give (2S)-isobutyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate as a crude pale yellow thick oil. The crude compound was taken forward without further purification.

Workup

customfor synthesizing naphthyl (aminoacid ester) phosphorochloridates

Sources & evidence

ORD record: ord-01f4de3f1ec5446fa281653c52750d37
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Linked notes

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