Ethanol → Enrasentan

HRID 650769Notes

Reaction equation

HRID 650769 reaction equation
O[C:2]1([C:38]2[CH:43]=[CH:42][C:41]3[O:44][CH2:45][O:46][C:40]=3[CH:39]=2)[C:10]2[C:5](=[CH:6][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:8][CH:9]=2)[C:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][C:16]=2[O:23][CH2:24][CH2:25][O:26]CC2C=CC=CC=2)=[C:3]1[C:34]([O:36]C)=[O:35].C(O)C>C(OC(=O)C)C>[OH:26][CH2:25][CH2:24][O:23][C:16]1[CH:17]=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[C@@H:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH3:14])[CH:6]=2)[C@H:2]([C:38]2[CH:43]=[CH:42][C:41]3[O:44][CH2:45][O:46][C:40]=3[CH:39]=2)[C@H:3]1[C:34]([OH:36])=[O:35]

Participants

4

Reactant 2

HCID 702EthanolHCID 67644849HCID 67644849, compound

Product 1

HCID 178103EnrasentanYield 83.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl (1SR)-1-hydroxy-3-[2-(2-benzyloxyeth-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxy phenyl)-5-propoxyindene-2-carboxylate (88 g, 0.141 moles) 10% palladium on carbon (21 g), 0.65 L of absolute ethanol and 0.65 L of ethylacetate was hydrogenated at 50 psi, 55° C. for 48 hrs. The catalyst was filtered off, and the filtrate concentrated in vacuo to give an amorphous glass. Crystallization from 35OmL of absolute ethanol gave 59.5 g (81%) of white solid; m.p. 165-168° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give an amorphous glass
  4. customCrystallization from 35OmL of absolute ethanol

Sources & evidence

ORD record
ord-0b7a4340d9304bd3addd83199495402d
Source dataset
uspto-grants-2001_08
Patent number
US06274737B1

Reaction notes

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