Dichloromethane → HCID 66779102, compound

HRID 408982Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:9])[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH2:5].[P:10](Cl)(Cl)(=[O:22])[O:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C(Cl)[Cl:26]>>[Cl:26][C:13]1[CH:14]=[CH:15][C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12]=1[O:11][P:10](=[N:5][C@@H:4]([CH:6]([CH3:8])[CH3:7])[C:3]([O:2][CH3:1])=[O:9])=[O:22]

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 94285Valine methyl ester

HCID 5756311-Dichlorophosphoryloxynaphthalene

Product 1

HCID 66779102HCID 66779102, compoundYield 62%

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates the hydrochloride salt of L-valine methyl ester (2.00 g, 11.93 mmol), naphthalen-1-yl phosphorodichloridate (0.77 g, 11.93 mmol) and TEA (4.11 mL, 23.85 mmol) in 20 mL of dry DCM, were combined to give (2S)-methyl 2-(chloro(naphthalen-1-yloxy)-phosphorylamino)-3-methylbutanoate in 62% yield (2.63 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record: ord-be6009e0c9fd4149b38a770b70950433
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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