1,2-Dimethoxyethane → 2-Hydroxy-1-[4-(2-{2-hydroxy-3-[(2-hydroxy-3-{2-[4-(2-hydroxy-2-methylpropionyl)-phenoxy]ethoxy}propyl)-(3-hydroxypropyl)amino]-propoxy}ethoxy)phenyl]-2-methylpropan-1-one

HRID 384586Notes

Reaction equation

HRID 384586 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[OH:6][C:7]([CH3:25])([CH3:24])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]2[CH2:23][O:22]2)=[CH:12][CH:11]=1)=[O:9].[CH3:26][O:27][CH2:28][CH2:29][O:30][CH3:31]>CC(O)C>[OH:6][C:7]([CH3:25])([CH3:24])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH:21]([OH:22])[CH2:23][N:1]([CH2:18][CH:17]([OH:16])[CH2:26][O:27][CH2:28][CH2:29][O:30][C:31]2[CH:12]=[CH:11][C:10]([C:8](=[O:9])[C:7]([OH:6])([CH3:24])[CH3:25])=[CH:15][CH:14]=2)[CH2:2][CH2:3][CH2:4][OH:5])=[CH:12][CH:11]=1)=[O:9]

Participants

5

Reactant 3

HCID 80711,2-Dimethoxyethane2×HCID 90863-Amino-1-propanolHCID 543951302-Hydroxy-2-methyl-1-[4-(2-oxiranylmethoxyethoxy)phenyl]propan-1-one

Product 1

HCID 576611722-Hydroxy-1-[4-(2-{2-hydroxy-3-[(2-hydroxy-3-{2-[4-(2-hydroxy-2-methylpropionyl)-phenoxy]ethoxy}propyl)-(3-hydroxypropyl)amino]-propoxy}ethoxy)phenyl]-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2.22 g (29.6 mmol) of 3-amino-1-propanol in 20 ml of 1,2-dimethoxyethane and 40 ml of 2-propanol is added a solution of 11.57 g (41.3 mmol) of the compound of Example 1A in 20 ml of 1,2-dimethoxyethane. The mixture is heated at reflux overnight. Solvent is evaporated to afford a mixture of the title compounds.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. customSolvent is evaporated
  4. customto afford

Sources & evidence

ORD record
ord-951aee0c875042d0abf622997d07f6c1
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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