Diethanolamine → HCID 58912940, compound

HRID 1829688Notes

Reaction equation

HRID 1829688 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. 1H NMR (300 MHz, CD3OD) δ 1.65 (m, 4H), 2.50 (m, 2H), 3.20 (m, 2H), 3.55 (m, 4H), 3.75 (m, 4H), 4.80 (s, 2H), 5.10 (s, 2H), 6.85 (d, 2H), 7.10 (d, 2H), 7.40 (m, 5H). m/z (ESI): 445 [C24H32N2O6+H]+.

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-914261c33f7c479fb614900ede495843
Source dataset
uspto-grants-2006_06
Patent number
US07064129B2

Reaction notes

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