Dichloromethane → HCID 66779267, compound

HRID 408983Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[CH:12]1([O:17][C:18](=[O:24])[C@@H:19]([NH2:23])[CH:20]([CH3:22])[CH3:21])[CH2:16][CH2:15][CH2:14][CH2:13]1.[P:25](Cl)(Cl)(=[O:37])[O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.C(N(CC)CC)C.[Cl:47]CCl>>[Cl:47][C:28]1[CH:29]=[CH:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]=1[O:26][P:25](=[N:23][C@@H:19]([CH:20]([CH3:22])[CH3:21])[C:18]([O:17][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:24])=[O:37]

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 59273156HCID 59273156, compound

Product 1

HCID 66779267HCID 66779267, compoundYield 72%

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates and tosylate salt of (S)-cyclopentyl-2-amino-3-methylbutanoate (2.58 g, 7.2 mmol), naphthalene-1-yl phosphorodichloridate (1.88 g, 7.2 mmol), triethyl amine (2.014 mL, 14.4 mmol) and dichloromethane (20 mL) were combined to give 2.12 g of desired (2S)-cyclopentyl 2-(chloro(naphthalen-1-yloxy)-phosphorylamino)-3-methylbutanoate as a pale yellow viscous oil in 72% yield.

Sources & evidence

ORD record: ord-633726a705904c528f0592bf3aaad2e6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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