Dichloromethane → HCID 86662578, compound

HRID 408990Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@H:13]([CH3:22])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15].[P:23](Cl)(Cl)(=[O:35])[O:24][C:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1.C(Cl)[Cl:39]>>[Cl:39][C:26]1[CH:27]=[CH:28][C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[O:24][P:23](=[N:12][C@H:13]([CH3:22])[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:15])=[O:35]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 86662579HCID 86662579, compound

Product 1

HCID 86662578HCID 86662578, compound

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (R)-neopentyl 2-aminopropanoate (3 g), naphthalene-1-yl phosphorodichloridate (2.36 g), TEA (2.52 mL) and DCM (90 mL) were combined to give (2R)-neopentyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate as a crude pale yellow thick oil. The crude compound was taken forward without further purification.

Sources & evidence

ORD record: ord-62943deac8c64852beffbaf2d4e4c1fa
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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