Chloride → HCID 178491610, compound

HRID 2225556Notes

Reaction equation

HRID 2225556 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][C:6]=1[O:15][CH3:16])(=O)C.C(O)(=O)[CH2:18][C:19]1[CH:27]=[CH:26][C:24](O)=[C:21](OC)[CH:20]=1.P(Cl)(OCC)(OCC)=O.[Cl-].C(=O)([O-])[O-].[K+].[K+].C([N:48](CC)CC)C>CN(C)C1C=CN=CC=1.CO.C(Cl)Cl>[CH3:18][C@H:19]1[CH2:27][CH2:26][C@H:24]([NH:48][C:12](=[O:14])[CH2:11][C:8]2[CH:9]=[CH:10][C:5]([OH:4])=[C:6]([O:15][CH3:16])[CH:7]=2)[CH2:21][CH2:20]1

Participants

10

Reactant 6

HCID 312ChlorideHCID 1738Homovanillic AcidHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 13139Diethyl chlorophosphateHCID 2264844-(Acetyloxy)-3-methoxybenzeneacetic acid

Product 1

HCID 178491610HCID 178491610, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Using 2.9 g of (4-acetoxy-3-methoxyphenyl)acetic acid derived from homovanillic acid by the acetylation thereof, 2.8 ml of diethyl chlorophosphate, 3.9 ml of triethylamine, 60 ml of methylene chloride, 2 g of trans-4-methylcyclohexylammmonium chloride, 0.6 g of 4-dimethylaminopyridine, 100 ml of methanol, and 5 g of potassium carbonate, a reaction similar to that conducted in Example 121 was carried out. The product obtained was recrystallized from methylene chloride/hexane, yielding 1.5 g of N-(trans-4-methylcyclohexyl)-2-(4-hydroxy-3-methoxyphenyl)acetamide (a compound of the present invention) as pale yellowish 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-7ade62ff73cb4c4db3adbac74b40426e
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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