Water → HCID 86749910, compound

HRID 864504Notes

Reaction equation

HRID 864504 reaction equation
[Si]([O:8][CH2:9][C@H:10]1[O:19][C@@H:18]2[C@@H:13]([S:14][C:15]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:16]=3[N:17]2[CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C@@H:12]([O:32][C:33](=[O:35])[CH3:34])[C@@H:11]1[O:36][C:37](=[O:39])[CH3:38])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:58]1CC[CH2:60][CH2:59]1.O.[C:64](OCC)(=[O:66])[CH3:65].CCCCCC>O1CCCC1>[C:33]([O:32][C@@H:12]1[C@@H:13]2[S:14][C:15]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:16]=3[N:17]([CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[C@@H:18]2[O:19][C@H:10]([CH2:9][O:8][C:59](=[O:58])[CH3:60])[C@H:11]1[OH:36])(=[O:35])[CH3:34].[C:37]([O:36][C@@H:11]1[C@@H:10]([CH2:9][O:8][C:64](=[O:66])[CH3:65])[O:19][C@@H:18]2[C@@H:13]([S:14][C:15]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:16]=3[N:17]2[CH2:20][CH2:21][N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])[C@H:12]1[OH:32])(=[O:39])[CH3:38]

Participants

7

Reactant 4

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 21226206Ethyl acetate hexaneHCID 131719595HCID 131719595, compound

Product 2

HCID 86749909HCID 86749909, compoundHCID 86749910HCID 86749910, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 2.54 g of the compound (15) obtained in Example 15 in 6 ml of tetrahydrofuran, 6 ml of a 1M solution of tetrabutylammoniumfluoride-tetrahydrofuran was added dropwise. The mixture was stirred for one hour at room temperature. Water was added to the reaction solution, and the mixture was extracted with chloroform, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography, and 580 mg (yield: 28.3 of the title compound (16) and 510 mg (yield 24.9%) of the title compound (17) were obtained from the fraction of ethyl acetate-hexane (4:1).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography, and 580 mg (yield

Sources & evidence

ORD record
ord-381a2d803bbb4fc0907342667538aa3e
Source dataset
uspto-grants-1996_10
Patent number
US05563137

Reaction notes

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