Ethyl bromoacetate → HCID 19040984, compound

HRID 1683819Notes

Reaction equation

[C:1]([C:3]1[CH:34]=[CH:33][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:31]=[CH:30][C:17]([C:18]([N:20]([CH:27]([CH3:29])[CH3:28])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:19])=[C:16]([OH:32])[CH:15]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].Br[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40]>CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:31]=[CH:30][C:17]([C:18]([N:20]([CH:27]([CH3:28])[CH3:29])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:19])=[C:16]([CH:15]=2)[O:32][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:33][CH:34]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A stirred solution of 4-[5-(4-cyanophenoxy)pentyloxy]-2-hydroxy-N-(1-methylethyl)-N-phenylbenzamide (250 mg, 0.55 mmol) in 2.5 mL of N,N-dimethylformamide is treated with 60% sodium hydride (22 mg, 0.55 mmol), and ethyl bromoacetate (67 μL, 0.60 mmol) and heated at 70° C. for 2.5 hours. The reaction is partitioned between ethyl acetate and water, dried over sodium sulfate and concentrated in vacuo to afford a yellow foam. This material is purified by chromatography on silica gel (30 g) with 50-70% ethyl acetate/hexane as the eluent to afford ethyl 5-[5-(4-cyanophenoxy)pentyloxy]-2-[N-(1-methylethyl)-N-phenylaminocarbonyl]phenoxyacetate as colorless foam.

Workup

customThe reaction is partitioned between ethyl acetate and water
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto afford a yellow foam
customThis material is purified by chromatography on silica gel (30 g) with 50-70% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record: ord-668126a13c344fc0aee4b94628e9ef00
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05639768

Reaction notes

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