Dichloromethane → HCID 86662580, compound

HRID 408992Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH2:22][CH2:23][S:24][CH3:25])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15].[P:26](Cl)(Cl)(=[O:38])[O:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][CH:29]=1.C(Cl)[Cl:42]>>[Cl:42][C:29]1[CH:30]=[CH:31][C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:28]=1[O:27][P:26](=[N:12][C@@H:13]([CH2:22][CH2:23][S:24][CH3:25])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:15])=[O:38]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 86662581HCID 86662581, compound

Product 1

HCID 86662580HCID 86662580, compoundYield 41%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (S)-neopentyl 2-amino-4-(methylthio)butanoate (2.00 g, 5.11 mmol), naphthalene-1-yl phosphorodichloridate (1.30 g, 5.11 mmol) and TEA (1.42 mL, 10.22 mmol) in 30 mL of dry DCM, were combined to give (2S)-neopentyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-4-(methylthio)butanoate in 41% yield (0.92 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record: ord-db4c93c746624bbfa81fa254bb16bc56
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

Loading…