Dichloromethane → HCID 66779469, compound

HRID 408978Notes

Reaction equation

S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH2:12][C@@H:13]([CH3:23])[C:14]([O:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:15].[P:24](Cl)(Cl)(=[O:36])[O:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.C(Cl)[Cl:40]>>[Cl:40][C:27]1[CH:28]=[CH:29][C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:26]=1[O:25][P:24](=[N:12][C@@H:13]([CH3:23])[C:14]([O:16][CH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)=[O:15])=[O:36]

Participants

Reactant 4

HCID 6344Dichloromethane

HCID 85570p-Toluenesulfonate

HCID 5756311-Dichlorophosphoryloxynaphthalene

HCID 53927162HCID 53927162, compound

Product 1

HCID 66779469HCID 66779469, compoundYield 70%

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates the tosylate salt of (S)-tetrahydro-2H-pyran-4-yl 2-aminopropanoate (1.00 g, 2.90 mmol), naphthalen-1-yl phosphorodichloridate (0.76 g, 2.90 mmol) and TEA (0.80 mL, 5.79 mmol) in 30 mL of dry DCM, were combined to give (2S)-tetrahydro-2H-pyran-4-yl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate in 70% yield (0.84 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record: ord-0f758a4e2771491a94a81f46787573f0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759318B2

Reaction notes

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