Diethanolamine → HCID 58912940, compound

HRID 2220907Notes

Reaction equation

HRID 2220907 reaction equation
C(O[C:4](=[O:28])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:9][CH:8]=1)C.[OH:29][CH2:30][CH2:31][NH:32][CH2:33][CH2:34][OH:35]>C(O)C>[CH2:21]([O:20][C:18](=[O:19])[NH:17][CH2:16][CH2:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4](=[O:28])[N:32]([CH2:33][CH2:34][OH:35])[CH2:31][CH2:30][OH:29])=[CH:12][CH:11]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 21031128[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester

Product 1

HCID 58912940HCID 58912940, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [4-(4-benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester 23 (0.3 g, 0.78 mmol), 2-(2-hydroxyethylamino)ethanol 24 (0.15 mL, 1.6 mmol), and ethanol (20 mL) was heated at 70° C. for 72 hours. Solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol, 100:5, v/v) to provide [4-(4-{[N,N-bis-(2-hydroxyethyl)carbamoyl]methoxy}phenyl)-butyl]carbamic acid benzyl ester 25 [0.19 g, 100% based on the recovered starting material (0.13 g)] as a pale yellow solid.

Workup

  1. customSolvent was evaporated in vacuo
  2. customThe residue was purified by flash chromatography (silica gel, dichloromethane/methanol, 100:5

Sources & evidence

ORD record
ord-f312fb602efb45b686b0691bd8d2f16d
Source dataset
uspto-grants-2008_05
Patent number
US07368447B2

Reaction notes

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