Hydrochloric Acid → HCID 69428068, compound

HRID 1295214Notes

Reaction equation

HRID 1295214 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][CH:16]=1.O[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].Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C1C=CN=CC=1)C.CN(C)C=O>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]([O:24][CH:26]([C:33](=[O:40])[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:23])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22344563HCID 22344563, compoundHCID 22930709HCID 22930709, compound

Product 1

HCID 69428068HCID 69428068, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of [4-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]acetic acid (1.00 g), methyl 4-hydroxy-5-oxo-5-phenylpentanoate (687 mg), 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (water-soluble carbodiimide; hereinafter to be referred to as WSC) (711 mg), 4-(N,N-dimethylamino)pyridine (75.5 mg) and N,N-dimethylformamide (10 ml) was stirred at room temperature for 18 hrs, and 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-(5-methyl-2-phenyl-4-oxazolylmethoxy)phenyl]acetoxy-5-oxo-5-phenylpentanoate (1.44 g, yield 88%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:2, 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-25ad24cf24b94b6d82ac61627160fa89
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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