Ammonium fluoride → HCID 11751411, compound

HRID 1866489Notes

Reaction equation

HRID 1866489 reaction equation
[F-].[NH4+].[Si]([O:10][C@H:11]([C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([CH2:41][OH:42])[CH:35]=1)[CH2:12][NH:13][C@H:14]([CH3:33])[CH2:15][C:16]1[CH:17]=[C:18]([CH2:22][C:23]([NH:25][CH:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:24])[CH:19]=[CH:20][CH:21]=1)(C(C)(C)C)(C)C>CO.O>[CH:26]1([NH:25][C:23](=[O:24])[CH2:22][C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([CH2:15][C@H:14]([NH:13][CH2:12][C@H:11]([OH:10])[C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([CH2:41][OH:42])[CH:35]=3)[CH3:33])[CH:17]=2)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

5

Reactant 2

HCID 25516Ammonium fluorideHCID 69023440HCID 69023440, compound

Product 1

HCID 11751411HCID 11751411, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Ammonium fluoride (98 mg, 2.64 mmol) was added in one portion to a stirred solution of 2-{3-[(2R)-2-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)propyl]phenyl}-N-cycloheptylacetamide (Preparation 1) (150 mg, 0.26 mmol) in methanol (3 ml) and water (1.5 ml) at room temperature. The reaction was heated at 40° C. for 18 hours and then allowed to cool to room temperature. The solvent was removed in vacuo and the residue dissolved in ethyl acetate (30 ml) and water (20 ml), the organic layer was separated, washed with brine (10 ml), dried (magnesium sulfate) and the solvent removed in vacuo to yield a clear oil. This was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol: ammonia (90:10:1 by volume) to furnish the title compound as a white foam (87 mg).

Workup

  1. temperatureto cool to room temperature
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate (30 ml)
  4. customwater (20 ml), the organic layer was separated
  5. washwashed with brine (10 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent removed in vacuo
  8. customto yield a clear oil
  9. customThis was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol: ammonia (90:10:1 by volume)

Sources & evidence

ORD record
ord-3c296634bbd14fbeb8cfafba5e879334
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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