Dichloromethane → HCID 86662575, compound

HRID 408989Notes

Reaction equation

S([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)([O-])(=O)=O.[CH2:12]([O:17][C:18](=[O:24])[CH:19]([NH2:23])[CH:20]([CH3:22])[CH3:21])[C:13]([CH3:16])([CH3:15])[CH3:14].[P:25](Cl)(Cl)(=[O:38])[O:26]OC1C=CC=C2C=1N=CC=C2.[CH2:41]([N:43](CC)CC)[CH3:42].[Cl:48]CCl>>[Cl:48][C:41]1[CH:42]=[CH:9][C:8]2[C:7](=[C:6]([O:38][P:25](=[N:23][C@@H:19]([CH:20]([CH3:21])[CH3:22])[C:18]([O:17][CH2:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:24])=[O:26])[CH:5]=[CH:11][CH:10]=2)[N:43]=1

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 8471Triethylamine

HCID 85570p-Toluenesulfonate

HCID 86662576HCID 86662576, compound

HCID 86662577HCID 86662577, compound

Product 1

HCID 86662575HCID 86662575, compound

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates, the tosylate salt of neopentyl-2-amino-3-methylbutanoate (1.2 g, 3.4 mmol), quinoline 8-yloxy phosphorodichloridate (900 mg, 3.4 mmol), triethyl amine (0.96 mL, 6.9 mmol) and dichloromethane (30 mL) were combined to give 3.1 g crude desired (2S)-neopentyl 2-(chloro(quinolin-8-yloxy)phosphorylamino)-3-methylbutanoate which was used directly to next step.

Workup

customfor synthesizing naphthyl (amino acid ester) phosphorochloridates

Sources & evidence

ORD record: ord-cb54c21adafd41b181c600e0f2fbd4e5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

Loading…