Ammonium fluoride → HCID 58959766, compound

HRID 916074Notes

Reaction equation

HRID 916074 reaction equation
[F-].[NH4+].[CH3:3][O:4][C:5](=[O:44])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C@H:15]([NH:17][CH2:18][C@H:19]([O:36][Si](C(C)(C)C)(C)C)[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:22]([CH2:34][OH:35])[CH:21]=2)[CH3:16])[CH:9]=1>O.CO>[NH3:17].[CH3:3][O:4][C:5](=[O:44])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C@H:15]([NH:17][CH2:18][C@@H:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[C:22]([CH2:34][OH:35])[CH:21]=2)[OH:36])[CH3:16])[CH:9]=1

Participants

6

Reactant 2

HCID 25516Ammonium fluorideHCID 68976934HCID 68976934, compound

Product 2

HCID 222AmmoniaHCID 58959766HCID 58959766, compoundYield 178%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Ammonium fluoride (2.80 g, 75.5 mmol) was added in one portion to a solution of methyl-3-(3-{(2R)-2-[(2R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-2-(4-[benzyloxy]-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-propanoate (Preparation 53) (4.47 g, 7.55 mmol) in water (20 ml) and methanol (30 ml) at room temperature. The reaction was heated at 40° C. for 18 hours and then allowed to cool to room temperature. The methanol was removed in vacuo and the resulting aqueous extracted with dichloromethane (3×75 ml), the combined organics were washed with water (25 ml), dried (sodium sulfate) and the solvent removed in vacuo to yield an orange foam. This was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol: 880 ammonia (95:5:0.5 by volume) to give the title compound as a yellow oil (3.21 g).

Workup

  1. temperatureto cool to room temperature
  2. customThe methanol was removed in vacuo
  3. extractionthe resulting aqueous extracted with dichloromethane (3×75 ml)
  4. washthe combined organics were washed with water (25 ml)
  5. dry with materialdried (sodium sulfate)
  6. customthe solvent removed in vacuo
  7. customto yield an orange foam
  8. customThis was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-d47d351c479d4c31b8308eafadcd538a
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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