Hydrochloric Acid → HCID 66780049, compound

HRID 408998Notes

Reaction equation

HRID 408998 reaction equation
[ClH:1].[NH2:2][C@@H:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:4]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5].[P:19](Cl)(Cl)(=[O:31])[O:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1>C(Cl)Cl>[CH:7]1([O:6][C:4](=[O:5])[C@@H:3]([N:2]=[P:19]([O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH:24]=[CH:23][C:22]=2[Cl:1])=[O:31])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 66778711HCID 66778711, compound

Product 1

HCID 66780049HCID 66780049, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the general procedure for synthesizing naphthyl (aminoacid ester) phosphorochloridates, the HCl salt of (S)-cyclohexyl 2-amino-2-phenylacetate (1 g), naphthalen-1-yl phosphorodichloridate (967 mg), TEA (1.03 mL) and DCM (30 mL) were combined to give (2S)-cyclohexyl-2-(chloro(naphthalen-1-yloxy)phosphorylamino)-2-phenylacetate in an 78% yield (1.32 g) as a pale yellow thick oil.

Workup

  1. customfor synthesizing naphthyl (aminoacid ester) phosphorochloridates

Sources & evidence

ORD record
ord-77c3475ecbd8429ea1de3d534b5ddf78
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

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