Methyl Ethyl Ketone → HCID 15106525, compound

HRID 847297Notes

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-4e571c5231e54cb882556d81423aa4b6
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05140046

Reaction notes

Loading…