Dichloromethane → HCID 66779010, compound

HRID 408991Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH2:25][CH2:26][S:27][CH3:28])[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:29](Cl)(Cl)(=[O:41])[O:30][C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C(Cl)[Cl:45]>>[Cl:45][C:32]1[CH:33]=[CH:34][C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:31]=1[O:30][P:29](=[N:12][C@@H:13]([CH2:25][CH2:26][S:27][CH3:28])[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:41]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 66779103HCID 66779103, compound

Product 1

HCID 66779010HCID 66779010, compoundYield 74%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-((S)-1-phenylethyl) 2-amino-4-(methylthio)butanoate (2.00 g, 4.70 mmol), naphthalene-1-yl phosphorodichloridate (1.23 g, 4.70 mmol) and TEA (1.31 mL, 9.40 mmol) in 30 mL of dry DCM, were combined to give (2S)-((S)-1-phenylethyl) 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-4-(methylthio)butanoate in 74% yield (1.67 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record: ord-ef933de4599949c38572d671a44cd0aa
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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