Hydrochloric Acid → HCID 69428124, compound

HRID 1295218Notes

Reaction equation

HRID 1295218 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:24])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20](OC)=[O:21])=[CH:15][CH:14]=2)[N:10]=1.[OH:25][CH:26]([C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:24])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:25][CH:26]([C:33](=[O:40])[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:21])=[CH:15][CH:14]=2)[N:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22930709HCID 22930709, compoundHCID 86591669HCID 86591669, compound

Product 1

HCID 69428124HCID 69428124, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl [4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetate (1.00 g), methyl 4-hydroxy-5-oxo-5-phenylpentanoate (709 mg), WSC (734 mg), 4-(N,N-dimethylamino)pyridine (77.9 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 6 hrs. The reaction mixture was poured into 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 4-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]phenyl]acetoxy-5-oxo-5-phenylpentanoate (1.56 g, yield %) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-44d7021b96294acc88cef09bd25fe86b
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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