Dichloromethane → HCID 86662584, compound

HRID 408994Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([C@H:22]([CH3:25])[CH2:23][CH3:24])[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]([C@H:22]([CH3:25])[CH2:23][CH3:24])[C:14]([O:16][CH2:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:15])=[O:38]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 86662585HCID 86662585, compound

Product 1

HCID 86662584HCID 86662584, compoundYield 37%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (2S,3R)-neopentyl 2-amino-3-methylpentanoate (2.5 g), naphthalen-1-yl phosphorodichloridate (1.75 g), TEA (1.86 mL) and DCM (50 mL) were combined to give (2S,3R)-neopentyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-3-methylpentanoate in a 37% yield (1.06 g) as a pale yellow thick oil.

Sources & evidence

ORD record: ord-7c339dfada9f4322af791a1a22abcda6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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