Diethyl chlorophosphate → HCID 178490193, compound

HRID 2225606Notes

Reaction equation

HRID 2225606 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH:8]=[CH:9][C:10]([OH:12])=O)(=[O:3])[CH3:2].C(O)(=O)/C=C/C1C=CC(OC)=C(O)C=1.P(Cl)(OCC)(OCC)=O.[Cl-].[CH3:42][C@H:43]1[CH2:48][CH2:47][C@H:46]([NH3+:49])[CH2:45][CH2:44]1>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(N(CC)CC)C>[CH3:42][C@H:43]1[CH2:48][CH2:47][C@H:46]([NH:49][C:10](=[O:12])[CH:9]=[CH:8][C:7]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH2:45][CH2:44]1

Participants

8

Reactant 4

HCID 13139Diethyl chlorophosphateHCID 736186Isoferulic AcidHCID 538974993-Acetoxy-4-methoxycinnamic acidHCID 178461400HCID 178461400, compound

Product 1

HCID 178490193HCID 178490193, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Using 5.9 g of 3-acetoxy-4-methoxycinnamic acid derived from isoferulic acid by the acetylation thereof, 4.34 ml of diethyl chlorophosphate, 8.35 ml of triethylamine, 500 ml of methylene chloride, 3.74 g of trans-4-methylcyclohexylammonium chloride, and 0.18 g of 4-dimethylaminopyridine, a reaction similar to that conducted in Example 104 was carried out. As a result, 6.3 g of N-(trans-4-methylcyclohexyl)-3-acetoxy-4-methoxycinnamamide (a compound of the present invention) was obtained as white crystal, which had the following physiochemical properties: Proton nuclear magnetic resonance spectrum (δ ppm in CDCl3):

Sources & evidence

ORD record
ord-ea2dce3d42604193832f9fb199082ded
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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