Dichloromethane → HCID 66779058, compound

HRID 408981Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH:25]([CH3:27])[CH3:26])[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:28](Cl)(Cl)(=[O:40])[O:29][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.C(Cl)[Cl:44]>>[C:19]1([C@@H:17]([O:16][C:14](=[O:15])[C@@H:13]([N:12]=[P:28]([O:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][C:31]=2[Cl:44])=[O:40])[CH:25]([CH3:27])[CH3:26])[CH3:18])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 66779054HCID 66779054, compound

Product 1

HCID 66779058HCID 66779058, compoundYield 96%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates, the tosylate salt of (S)-((S)-1-phenylethyl) 2-amino-3-methylbutanoate (2 g), naphthalen-1-yl phosphorodichloridate (1.33 g), TEA (1.41 mL) and DCM (60 mL) were combined to give (2S)-((S)-1-phenylethyl)-2-(chloro(naphthalen-1-yloxy)phosphorylamino)-3-methylbutanoate in an 96% yield (2.17 g) as a pale yellow thick oil.

Workup

customfor synthesizing naphthyl (aminoacid ester) phosphorochloridates

Sources & evidence

ORD record: ord-07af95301ad04d97a2629e3e1a5e9348
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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