Dichloromethane → HCID 86662589, compound

HRID 409001Notes

Reaction equation

HRID 409001 reaction equation
[NH2:1][C@H:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH2:7][CH3:8])=[O:4].[P:15](Cl)(Cl)(=[O:27])[O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(Cl)[Cl:31]>>[Cl:31][C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:17]=1[O:16][P:15](=[N:1][C@H:2]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH2:7][CH3:8])=[O:4])=[O:27]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 6997196HCID 6997196, compound

Product 1

HCID 86662589HCID 86662589, compoundYield 59%

Procedure

Using the general procedure for synthesizing naphthyl (amino acid ester) phosphorochloridates the hydrochloride salt of (R)-propyl 2-amino-2-phenylacetate (2.00 g, 8.71 mmol), naphthalen-1-yl phosphorodichloridate (2.27, 8.71 mmol) and TEA (2.42 mL, 17.41 mmol) were combined in 20 mL of dry DCM, to give (2R)-propyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in 59% yield (2.15 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record
ord-26a31bd549bd4729a23add66232b5da1
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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