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

HRID 409004Notes

Reaction equation

S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:25])[C:14]([O:16][C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])=[O:15].[P:26](Cl)(Cl)(=[O:39])[O:27]OC1C2C(=CC=CC=2)C=CC=1.C(N([CH2:47][CH3:48])CC)C.Cl[CH2:50][Cl:51]>>[Cl:51][C:50]1[CH:48]=[CH:47][C:10]2[C:8](=[CH:7][CH:6]=[CH:5][CH:11]=2)[C:9]=1[O:39][P:26](=[N:12][C@@H:13]([CH3:25])[C:14]([O:16][C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18])=[O:15])=[O:27]

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 85570p-Toluenesulfonate

HCID 66778863(S)-((S)-1-phenylethyl) 2-aminopropanoate

HCID 86662592Naphthalen-1-yloxy phosphorodichloridate

Product 1

HCID 66778689(2S)-((S)-1-phenylethyl) 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoateYield 26%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-((S)-1-phenylethyl) 2-aminopropanoate (1.05 g, 2.85 mmol), naphthalen-1-yloxy phosphorodichloridate (2.85 mmol), triethyl amine (0.76 mL, 5.56 mmol) and dichloromethane (20 mL) were combined to give 610 g of desired (2S)-((S)-1-phenylethyl) 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate in 26% yield as pale yellow oil.

Sources & evidence

ORD record: ord-026a6128d24b43e8b5adfc018e29ddb5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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