Water → HCID 59586728, compound

HRID 218539Notes

Reaction equation

HRID 218539 reaction equation
[Si]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:37][C@H:36]([CH2:38][NH:39][C:40]([C:42]4[S:43][C:44]([Cl:47])=[CH:45][CH:46]=4)=[O:41])[O:35][C:34]3=[O:48])=[CH:29][C:28]=2[CH3:49])[C:22]1=[O:50])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[Cl-].[Na+]>C1COCC1.C(OCC)(=O)C>[Cl:47][C:44]1[S:43][C:42]([C:40]([NH:39][CH2:38][C@@H:36]2[O:35][C:34](=[O:48])[N:33]([C:30]3[CH:31]=[CH:32][C:27]([N:23]4[CH2:24][CH2:25][CH2:26][N:21]([CH2:20][CH2:19][OH:18])[C:22]4=[O:50])=[C:28]([CH3:49])[CH:29]=3)[CH2:37]2)=[O:41])=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 59586698HCID 59586698, compound

Product 1

HCID 59586728HCID 59586728, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 232 mg (0.32 mmol) of the product from example 67A in 6 ml of THF is admixed with 195 mg (0.74 mmol) of a 1 molar solution of tetrabutylammonium fluoride in THF. The mixture is stirred at RT for 2 h. Then it is admixed with 60 ml of water, 30 ml of ethyl acetate and 6 ml of sodium chloride solution, and the phases are separated. The organic phase is extracted three times with ethyl acetate and the combined organic phases are dried over sodium sulfate. After filtration, the mixture is freed of the solvent and the residue is prepurified by chromatography on silica gel (20:1 dichloromethane/methanol). Subsequent purification by means of preparative HPLC with an acetonitrile/water mixture affords 29 mg (18% of theory) of the desired product.

Workup

  1. customthe phases are separated
  2. extractionThe organic phase is extracted three times with ethyl acetate
  3. dry with materialthe combined organic phases are dried over sodium sulfate
  4. filtrationAfter filtration
  5. customSubsequent purification by means of preparative HPLC with an acetonitrile/water mixture

Sources & evidence

ORD record
ord-6454c7d939444816a7950424c57e6dd8
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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