Water → Fumarate

HRID 638033Notes

Reaction equation

HRID 638033 reaction equation
C([N:8]([CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([OH:47])=[C:43]([C:48](=[O:50])[NH2:49])[CH:42]=1)[CH2:9][CH:10]([OH:37])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([CH3:30])[N:22]=[C:21]([CH3:31])[C:20]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:15][CH:14]=1)C1C=CC=CC=1.[C:51]([OH:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([OH:56])=[O:55].O>C(O)(C)C>[C:48]([C:43]1[CH:42]=[C:41]([CH:46]=[CH:45][C:44]=1[OH:47])[O:40][CH2:39][CH2:38][NH:8][CH2:9][CH:10]([OH:37])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([CH3:30])[N:22]=[C:21]([CH3:31])[C:20]=2[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:15][CH:14]=1)(=[O:50])[NH2:49].[C:51]([O-:58])(=[O:57])/[CH:52]=[CH:53]/[C:54]([O-:56])=[O:55]

Participants

6

Reactant 3

HCID 962WaterHCID 444972Fumaric AcidHCID 53924858HCID 53924858, compound

Product 2

HCID 5460307FumarateHCID 20255149HCID 20255149, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

11.6 g of 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(3,5-dicarboethoxy-2,6-dimethylpyridin-4-yl)-phenoxy]-2-propanol are hydrogenated and worked up analogously to Example 1. The resulting base is reacted with fumaric acid in isopropanol and the resulting salt is recrystallised from ethanol. After drying for 15 hours at 0.05 mm Hg and 80°, 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(3,5-dicarboethoxy-2,6-dimethylpyridin-4-yl)-phenoxy]-2-propanol is obtained in the form of a neutral fumarate with 1/4 mole of water of crystallisation and has a melting point of 133°-135°.

Workup

  1. customthe resulting salt is recrystallised from ethanol
  2. customAfter drying for 15 hours at 0.05 mm Hg and 80°

Sources & evidence

ORD record
ord-155d5b07eb474e3fbc655ef47b0aad0a
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

Loading…