Diethanolamine → HCID 58912940, compound

HRID 254381Notes

Reaction equation

HRID 254381 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 480 (0.3 g, 0.78 mmol), 2-(2-hydroxyethylamino)ethanol (0.15 m-L, 1.6 mmol), and ethanol (20 mL) was heated at 70° C. for 72 hours. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, dichloromethane/methanol, 100:5-1, v/v) to provide 490 (0.19 g, 100% based on the recovered starting material (0.13 g)) as a pale yellow solid. 1H NMR (300 MHz, CDCl3) δ 1.55 (m, 4H), 2.56 (t, 2H), 3.20 (q, 2H), 3.60 (m, 4H), 3.90 (m, 2H), 3.96 (m, 2H), 4.85 (s, 2H), 5.09 (s, 2H), 6.85 (d, 2H), 7.06 (d, 2H), 7.40 (m, 5H). m/z (ESI) 445.

Workup

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

Sources & evidence

ORD record
ord-1da8ee88ea2040b2988a0c0f8de12bd5
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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