Tetrabutylammonium Fluoride Trihydrate → 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(3-carbamoyl-propyl)]-amide

HRID 2256738Notes

Reaction equation

HRID 2256738 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:22]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:71])[C@H:30]([CH3:70])[CH2:31][C@H:32]([O:62][Si](C(C)(C)C)(C)C)[C@@H:33]([NH:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:34][C@@H:35]([CH:51]([CH3:53])[CH3:52])[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH2:46][CH2:47][CH2:48][O:49][CH3:50])[CH:38]=1)(=[O:24])[NH2:23]>CN(C)C=O>[C:22]([CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:71])[C@H:30]([CH3:70])[CH2:31][C@H:32]([OH:62])[C@@H:33]([NH:54][C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56])[CH2:34][C@@H:35]([CH:51]([CH3:53])[CH3:52])[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([O:45][CH2:46][CH2:47][CH2:48][O:49][CH3:50])[CH:38]=1)(=[O:24])[NH2:23]

Participants

4

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 542315885(S)-Tert-butoxycarbonylamino-4(S)-tert-butyldimethylsilyloxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(3-carbamoylpropyl)]-amide

Product 1

HCID 542998385(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid [N-(3-carbamoyl-propyl)]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg of tetrabutylammonium fluoride trihydrate are added to 115 mg of 5(S)-tert-butoxycarbonylamino-4(S)-tert-butyldimethylsilyloxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxy-propyloxy)-phenyl]-octanoic acid [N-(3-carbamoyl-propyl)]-amide in 4 ml of dimethylformamide at 0° C. The reaction mixture is stirred for a further 5 hours at room temperature and then concentrated by evaporation. 20 ml of sainted sodium hydrogen carbonate solution are added to the evaporation residue and the mixture is extracted repeatedly with ethyl acetate. The organic phases are washed with saturated sodium chloride solution and concentrated by evaporation. The residue is purified by means of FC (18 g of silica gel, dichloromethane/methanol=9:1). The title compound is obtained: Rf (dichloromethane/methanol=9:1)=0.24.

Workup

  1. concentrationconcentrated by evaporation
  2. addition20 ml of sainted sodium hydrogen carbonate solution are added to the evaporation residue
  3. extractionthe mixture is extracted repeatedly with ethyl acetate
  4. washThe organic phases are washed with saturated sodium chloride solution
  5. concentrationconcentrated by evaporation
  6. customThe residue is purified by means of FC (18 g of silica gel, dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-b4a1c86e86384f54bdff3a5b4fd8af74
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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