Water → HCID 59586696, compound

HRID 218540Notes

Reaction equation

HRID 218540 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28]([C:30]4[S:31][C:32]([Cl:35])=[CH:33][CH:34]=4)=[O:29])[O:23][C:22]3=[O:36])=[CH:17][C:16]=2[Cl:37])[C:10]1=[O:38])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.[Cl-].[Na+]>C1COCC1.C(OCC)(=O)C>[Cl:35][C:32]1[S:31][C:30]([C:28]([NH:27][CH2:26][C@@H:24]2[O:23][C:22](=[O:36])[N:21]([C:18]3[CH:19]=[CH:20][C:15]([N:11]4[CH2:12][CH2:13][CH2:14][N:9]([CH2:8][CH2:7][OH:6])[C:10]4=[O:38])=[C:16]([Cl:37])[CH:17]=3)[CH2:25]2)=[O:29])=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 59586724HCID 59586724, compound

Product 1

HCID 59586696HCID 59586696, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 355 mg (0.47 mmol) of the product from example 70A in 9 ml of THF is admixed with 290 mg (1.10 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 80 ml of water, 50 ml of ethyl acetate and 6 ml of sodium chloride solution, and the phases are separated. The organic phase is extracted twice 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 39 mg (16% of theory) of the desired product.

Workup

  1. customthe phases are separated
  2. extractionThe organic phase is extracted twice 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-2c509b7c7e6b49e6bbc1e3973c03acde
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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