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 744825Notes

Reaction equation

HRID 744825 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 saturated 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 saturated 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-e326e8a4bc9245c9b3ef1c2148cd70b5
Source dataset
uspto-grants-1996_09
Patent number
US05559111

Reaction notes

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