Dichloromethane → HCID 86662588, compound

HRID 409000Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@H:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[P:30](Cl)(Cl)(=[O:42])[O:31][C:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][CH:33]=1.C(Cl)[Cl:46]>>[Cl:46][C:33]1[CH:34]=[CH:35][C:36]2[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:32]=1[O:31][P:30](=[N:12][C@H:13]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[O:42]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 10911681HCID 10911681, compound

Product 1

HCID 86662588HCID 86662588, compoundYield 72%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the tosylate salt of (R)-benzyl 2-amino-2-phenylacetate (1.50 g, 3.63 mmol), and naphthalen-1-yl phosphorodichloridate (0.95 g, 3.63 mmol) and TEA (1.01 mL, 7.26 mmol) in 20 mL of dry DCM, were combined to give (2R)-benzyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in 72% yield (1.21 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record: ord-0498255f2fb64028b228e5c1fb89c303
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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