Acetic Anhydride → HCID 20583566, compound

HRID 411760Notes

Reaction equation

HRID 411760 reaction equation
[OH:1][C@@H:2]1[C@:10]2([CH3:11])[C@H:5]([CH2:6][C@@H:7]([C:35]3[CH:40]=[CH:39][C:38]([O:41][CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][O:43]4)=[CH:37][CH:36]=3)[C@@H:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][C:28]([F:34])([F:33])[C:29]([F:32])([F:31])[F:30])=[CH:14][CH:13]=3)[CH2:9]2)[CH2:4][CH2:3]1.[C:48](OC(=O)C)(=[O:50])[CH3:49].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:48]([O:1][C@@H:2]1[C@:10]2([CH3:11])[C@H:5]([CH2:6][C@@H:7]([C:35]3[CH:36]=[CH:37][C:38]([O:41][CH:42]4[CH2:47][CH2:46][CH2:45][CH2:44][O:43]4)=[CH:39][CH:40]=3)[C@@H:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24][CH2:25][CH2:26][CH2:27][C:28]([F:33])([F:34])[C:29]([F:30])([F:31])[F:32])=[CH:14][CH:13]=3)[CH2:9]2)[CH2:4][CH2:3]1)(=[O:50])[CH3:49]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 20583568HCID 20583568, compound

Product 1

HCID 20583566HCID 20583566, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The solution of 1.43 g (2.51 mmol) of the compound that is presented in Example 2c is reacted analogously to Example 1, and after working-up, a mixture that consists of the title compound is isolated, and (1S,3S,4R,6S,9S)-9-hydroxy-4-[4-(tetrahydropyran-2-yloxy)phenyl]-1-methyl-3-[4-(10,10,11,11,11-pentafluoro-6-thia-undecyloxy)phenyl]-bicyclo[4.3.0]nonane, which is dissolved in 25 ml of anhydrous pyridine, is mixed with 3 ml of acetic anhydride and a spatula tip full of 4-dimethylaminopyridine, and it is stirred for 2 hours at 23° C. It is poured into saturated sodium bicarbonate solution, extracted several times with dichloromethane, the combined organic extracts are washed with saturated sodium chloride solution and dried on sodium sulfate. The residue that is obtained after filtration and removal of the solvent is purified by chromatography on about 400 ml of fine silica gel with a gradient system that consists of n-hexane and ethyl acetate. 1.57 g (2.16 mmol, 86%) of the title compound is isolated as a colorless foam.

Workup

  1. customis isolated
  2. extractionextracted several times with dichloromethane
  3. washthe combined organic extracts are washed with saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. customThe residue that is obtained
  6. filtrationafter filtration and removal of the solvent
  7. customis purified by chromatography on about 400 ml of fine silica gel with a gradient system that

Sources & evidence

ORD record
ord-55fecaf28a654adab75b2326e3f2d7e6
Source dataset
uspto-grants-2003_05
Patent number
US06559181B1

Reaction notes

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