Dichloromethane → HCID 66778834, compound

HRID 409003Notes

Reaction equation

HRID 409003 reaction equation
[NH2:1][C@H:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:4].[P:18](Cl)(Cl)(=[O:30])[O:19][C:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1.C(Cl)[Cl:34]>>[Cl:34][C:21]1[CH:22]=[CH:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]=1[O:19][P:18](=[N:1][C@H:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]([O:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:4])=[O:30]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 61277994HCID 61277994, compound

Product 1

HCID 66778834HCID 66778834, compoundYield 60%

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates the hydrochloride salt of (R)-cyclohexyl 2-amino-2-phenylacetate (2.00 g, 7.41 mmol), naphthalen-1-yl phosphorodichloridate (1.94 g, 7.41 mmol) and TEA (2.06 mL, 14.83 mmol) were combined in 15 mL of dry DCM, to give (2R)-cyclohexyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in 60% yield (2.75 g), as a clear, yellow, thick oil.

Sources & evidence

ORD record
ord-38f5374ccdf349f48c92b8c473226eb4
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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