Methyl Ethyl Ketone → HCID 15106525, compound

HRID 1197105Notes

Reaction equation

[OH:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=[O:9])=[C:4]([NH:13][C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:17][CH:16]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42].CC(=O)CC.[C:51]([O:54][CH2:55][CH3:56])(=[O:53])[CH3:52]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:44]([O:43][C:41]([CH2:40][O:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([O:10][CH2:52][C:51]([O:54][CH2:55][CH3:56])=[O:53])=[O:9])=[C:4]([NH:13][C:14](=[O:32])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:17][CH:16]=2)[CH:3]=1)=[O:42])[CH3:45]

Participants

Conditions

Temperature: 60 °C

Procedure

A catalytic amount of tetra-n-butylammonium bromide was added to a mixture of 0.64 g of 4-hydroxy-2-[p-(4-phenylbutoxy)benzamido]phenoxyacetic acid obtained in Example 78, 0.50 g of anhydrous potassium carbonate, 0.60 g of ethyl bromoacetate and 8 ml of 2-butanone followed by stirring at 60° C. for 4 hours. The reaction mixture was diluted with ethyl acetate and insoluble materials were filtered off. After the filtrate was washed with water and dried over anhydrous magnesium sulfate, the solvent was distilled off. The obtained solid was recrystallized from ethanol to obtain 0.83 g of ethyl [[4-ethoxycarbonylmethoxy-2-[p-(4-phenylbutoxy)benzamido] phenoxy]acetoxy]acetate.

Workup

filtrationwere filtered off
washAfter the filtrate was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off
customThe obtained solid was recrystallized from ethanol

Sources & evidence

ORD record: ord-a4e16f3d3cd6455ea24d1c1924ba636b
Source dataset: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05116853

Reaction notes

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