Dichloromethane → HCID 66779802, compound

HRID 408972

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:23])[C:14]([O:16][CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15].[P:24](Cl)(Cl)(=[O:36])[O:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.C(Cl)[Cl:40]>>[Cl:40][C:27]1[CH:28]=[CH:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]=1[O:25][P:24](=[N:12][C@@H:13]([CH3:23])[C:14]([O:16][CH2:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])=[O:36]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 54188349(S)-3,3-dimethylbutyl 2-aminopropanoate

Product 1

HCID 66779802HCID 66779802, compoundYield 91%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-3,3-dimethylbutyl 2-aminopropanoate (2.00 g, 5.79 mmol), naphthalen-1-yl phosphorodichloridate (1.51 g, 5.79 mmol) and TEA (1.61 mL, 11.58 mmol) in 30 mL of dry DCM, were combined to give (2S)-3,3-dimethylbutyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate in 91% yield (2.10 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record: ord-bade8866a5f54369866d0f1a6f6fedd5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Linked notes

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