Dichloromethane → (2S)-2,3-dihydro-1H-inden-2-yl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate

HRID 408970Notizen

Reaktionsgleichung

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:26])[C:14]([O:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:15].[P:27](Cl)(Cl)(=[O:39])[O:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.C(Cl)[Cl:43]>>[Cl:43][C:30]1[CH:31]=[CH:32][C:33]2[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:29]=1[O:28][P:27](=[N:12][C@@H:13]([CH3:26])[C:14]([O:16][CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18]1)=[O:15])=[O:39]

Komponenten

Edukt 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 66780036(S)-2,3-dihydro-1H-inden-2-yl 2-aminopropanoate

Produkt 1

HCID 66779638(2S)-2,3-dihydro-1H-inden-2-yl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoateAusbeute 65 %

Versuchsvorschrift

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-2,3-dihydro-1H-inden-2-yl 2-aminopropanoate (2.00 g, 5.30 mmol), naphthalen-1-yl phosphorodichloridate (1.38 g, 5.30 mmol) and TEA (1.48 mL, 10.60 mmol) in 30 mL of dry DCM, were combined to give (2S)-2,3-dihydro-1H-inden-2-yl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate in 65% yield (1.48 g), as a yellow, thick oil.

Quellen und Nachweise

ORD-Eintrag: ord-d86dc1344eae4028b02c44fcf5a28354
Quelldatensatz: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08759318B2

Notizen zur Reaktion

Wird geladen…