Chloride → HCID 178475399, compound

HRID 2225555

Reaction equation

HRID 2225555 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][C:17](=[O:19])[CH3:18])[CH:8]=[CH:9][C:10]([OH:12])=O)(=[O:3])[CH3:2].C(O)(=O)/C=[CH:22]/[C:23]1[CH:30]=[CH:29][C:27](O)=[C:25](O)[CH:24]=1.P(Cl)(OCC)(OCC)=O.[Cl-].C([N:45](CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:22][C@H:23]1[CH2:30][CH2:29][C@H:27]([NH:45][C:10](=[O:12])[CH:9]=[CH:8][C:7]2[CH:13]=[CH:14][C:15]([O:16][C:17](=[O:19])[CH3:18])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH2:25][CH2:24]1

Participants

8

Reactant 5

HCID 312ChlorideHCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 991033,4-Diacetoxycinnamic acidHCID 689043Caffeic Acid

Product 1

HCID 178475399HCID 178475399, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Using 3.4 g of 3,4-diacetoxycinnamic acid derived from caffeic acid by the acetylation thereof, 2.8 ml of diethyl chlorophosphate, 3.9 ml of triethylamine, 2 g of trans-4-methylcyclohexylammmonium chloride, 60 ml of methylene chloride, and 0.6 g of 4-dimethylaminopyridine, a reaction similar to that conducted in Example 81 was carried out. The product obtained was recrystallized from methylene chloride/hexane, yielding 3.19 g of N-(trans-4-methylcyclohexyl)-3,4-diacetoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe product obtained
  2. customwas recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-7b88b2ba4e274b3aaba3547fb5951e4c
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Linked notes

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