Diethyl iminodiacetate → N-(2-ethoxy-2-oxoethyl)-N-[5-[[6-([1,1'-biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy) benzoyl]glycine ethyl ester

HRID 488325Notes

Reaction equation

HRID 488325 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:19]([CH:23]=2)[C:20](Cl)=[O:21])=[CH:3][CH:2]=1.[NH:38]([CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41]>C(OCC)(=O)C.CCCCCC>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][N:38]([CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])[C:20](=[O:21])[C:19]1[CH:23]=[C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:4]2[CH:5]=[CH:6][C:1]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:2][CH:3]=2)[CH:16]=[CH:17][C:18]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:44]

Participants

4

Reactant 2

HCID 80502Diethyl iminodiacetateHCID 53865506HCID 53865506, compound

Product 1

HCID 19091786N-(2-ethoxy-2-oxoethyl)-N-[5-[[6-([1,1'-biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy) benzoyl]glycine ethyl esterYield 74%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The reaction of 5-[[6-([1,1'-biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy)benzoic acid chloride with diethyl iminodiacetate under conditions described in Example 80 gave, after purification by HPLC using 25% ethyl acetate-hexane, N-(2-ethoxy-2-oxoethyl)-N-[5-[[6-([1,1'-biphenyl]-4-yloxy)hexyl]oxy]-2-(phenylmethoxy) benzoyl]glycine ethyl ester (74% yield, mp 60°-62° ). The structure was confirmed by nmr and mass spectra.

Workup

  1. customgave
  2. customafter purification by HPLC

Sources & evidence

ORD record
ord-6139681721a7472588a3ae0918464f2c
Source dataset
uspto-grants-1994_03
Patent number
US05298652

Reaction notes

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