Dichloromethane → HCID 86662572, compound

HRID 408987Notes

Reaction equation

S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH:26]([CH3:28])[CH3:27])[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])=[O:15].[P:29](Cl)(Cl)(=[O:42])[O:30]OC1C=C2C(=CC=1)N=CC=C2.[CH2:45]([N:47](CC)CC)[CH3:46].[Cl:52]CCl>>[Cl:52][C:45]1[CH:46]=[CH:9][C:8]2[C:7](=[CH:6][CH:5]=[C:11]([O:42][P:29](=[N:12][C@@H:13]([CH:26]([CH3:28])[CH3:27])[C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=3[F:25])=[O:15])=[O:30])[CH:10]=2)[N:47]=1

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 85570p-Toluenesulfonate

HCID 66778986HCID 66778986, compound

HCID 86662573HCID 86662573, compound

Product 1

HCID 86662572HCID 86662572, compoundYield 24%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-2,4-difluorobenzyl 2-amino-3-methylbutanoate (1.7 g, 4.1 mmol), quinoline 6-yloxy phosphorodichloridate (1.08 g, 4.1 mmol), triethyl amine (1.15 mL, 8.2 mmol) and dichloromethane (30 mL) were combined to give 462 mg of desired (2S)-2,4-difluorobenzyl 2-(chloro(quinolin-6-yloxy)phosphorylamino)-3-methylbutanoate after short silica gel chromatography as pale yellow gummy syrup in 24% yield.

Sources & evidence

ORD record: ord-d1e8a8b493724ea4825528a36b951417
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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