HCID 178455551, compound → HCID 178455550, compound

HRID 272255Notes

Reaction equation

HRID 272255 reaction equation
C([O:8][C:9]1[CH:41]=[CH:40][C:12]([O:13][CH2:14][C@@H:15]([OH:39])[CH2:16][NH:17][C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]3[CH:38]=[CH:37][C:27]([O:28][C:29]([CH3:36])([CH3:35])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)=[CH:11][C:10]=1[S:42]([CH2:44][CH2:45][CH2:46][CH3:47])=[O:43])C1C=CC=CC=1>FC(F)(F)C(O)=O>[CH2:44]([S:42]([C:10]1[CH:11]=[C:12]([CH:40]=[CH:41][C:9]=1[OH:8])[O:13][CH2:14][C@@H:15]([OH:39])[CH2:16][NH:17][C@H:18]1[CH2:23][CH2:22][C@H:21]([C:24]2[CH:25]=[CH:26][C:27]([O:28][C:29]([CH3:35])([CH3:36])[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:37][CH:38]=2)[CH2:20][CH2:19]1)=[O:43])[CH2:45][CH2:46][CH3:47]

Participants

3

Reactant 1

HCID 178455551HCID 178455551, compound

Product 1

HCID 178455550HCID 178455550, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.720 g of ethyl trans-2-{4-[4-({(2S)-3-[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]-2-hydroxypropyl}amino)cyclohexyl]phenoxy}-2,2-dimethylacetate (1.08 mmol) in trifluoroacetic acid (12 ml) is heated at 60° C. for 3 hours. The solvent is evaporated and the residue is treated with a sodium bicarbonate solution and ethyl acetate. The organic phase is separated, dried, filtered and evaporated under vacuum. The product thus obtained is purified by flash chromatography, elution being carried out with a methylene chloride/methanol/aqueous ammonia (9/1/0.1) mixture. The title product is obtained in the form of a solid (0.31 g, 50%).

Workup

  1. customThe solvent is evaporated
  2. additionthe residue is treated with a sodium bicarbonate solution and ethyl acetate
  3. customThe organic phase is separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe product thus obtained
  8. customis purified by flash chromatography, elution

Sources & evidence

ORD record
ord-54f5559dafcd4f748b5e93fd19d676cb
Source dataset
uspto-grants-2008_11
Patent number
US07453010B2

Reaction notes

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