Dicyclohexylcarbodiimide → 4-(Acetylamino)benzoic acid, 4-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-2-pentenyl ester

HRID 1199298Notes

Reaction equation

HRID 1199298 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([O:12][C:13]1[CH:25]=[CH:24][C:16]([O:17][CH:18]([CH3:23])[CH:19]=[CH:20][CH2:21][OH:22])=[CH:15][CH:14]=1)[CH:6]=[N:5]2.[C:26]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)(=[O:28])[CH3:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O.CCOCC.O>[C:26]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([O:22][CH2:21][CH:20]=[CH:19][CH:18]([O:17][C:16]2[CH:15]=[CH:14][C:13]([O:12][C:7]3[CH:6]=[N:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=4)[N:8]=3)=[CH:25][CH:24]=2)[CH3:23])=[O:35])=[CH:32][CH:31]=1)(=[O:28])[CH3:27]

Participants

8

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19266p-Acetamidobenzoic acidHCID 542751324-(4-((6-Chloro-2-quinoxalinyl)oxy)phenoxy)2-penten-1-ol

Product 1

HCID 571706794-(Acetylamino)benzoic acid, 4-(4-((6-chloro-2-quinoxalinyl)oxy)phenoxy)-2-pentenyl esterYield 27.6%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.5 g (4.2 mmol) of the pentenol obtained in Example 3 above, 0.82 g (4.6 mmol) of 4-(acetylamino)benzoic acid, 0.95 g (4.6 mmol) of dicyclohexylcarbodiimide and 0.05 g of 4-(dimethylamino)pyridine in 20 ml of dimethylformamide was stirred at room temperature for 72 hours. The mixture was diluted with ether and water and filtered. The filtrates were separated, and the organic layer washed with saturated aqueous NaHCO3 and water, dried over MgSO4 and evaporated to dryness. The residue was purified by preparative scale HPLC, eluting with a 65:35 hexane:acetone mixture to give 0.6 g of the desired product as a pale yellow, glassy solid, m.p. 62°-68° C. (Compound 23).

Workup

  1. filtrationfiltered
  2. customThe filtrates were separated
  3. washthe organic layer washed with saturated aqueous NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe residue was purified by preparative scale HPLC
  7. washeluting with a 65:35 hexane

Sources & evidence

ORD record
ord-f3b539fb4a5b4ee19f4a905e5d847f8d
Source dataset
uspto-grants-1990_02
Patent number
US04900354

Reaction notes

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