Ammonium fluoride → HCID 57978278, compound

HRID 1866516Notes

Reaction equation

HRID 1866516 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][NH:14][CH2:15][C@@H:16]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:27]([CH2:39][OH:40])[CH:26]=2)[O:17][Si](C(C)(C)C)(C)C)[CH:7]=1)[CH3:2].[F-].[NH4+]>CO.O>[NH3:14].[CH2:32]([O:31][C:28]1[CH:29]=[CH:30][C:25]([C@@H:16]([OH:17])[CH2:15][NH:14][CH2:13][CH2:12][C:8]2[CH:7]=[C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:41])[CH:11]=[CH:10][CH:9]=2)=[CH:26][C:27]=1[CH2:39][OH:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 2

HCID 25516Ammonium fluorideHCID 70946576HCID 70946576, compound

Product 2

HCID 222AmmoniaHCID 57978278HCID 57978278, compoundYield 198%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl(3-{2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]ethyl}phenyl)acetate (Preparation 54) (2.39 g, 4.14 mmol) in methanol (15 ml) and water (10 ml) was treated with ammonium fluoride (1.53 g, 41.4 mmol) and the reaction heated to 40° C. for 16 hours. The methanol was removed in vacuo and the aqueous residue extracted with dichloromethane (3×50 ml). The combined organics were dried (sodium sulfate) and the sovent removed in vacuo and the residue purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (97:3:0.3 changing to 95:5:0.5, by volume) to give the title compound as an orange gum (1.90 g).

Workup

  1. customThe methanol was removed in vacuo
  2. extractionthe aqueous residue extracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organics were dried (sodium sulfate)
  4. customthe sovent removed in vacuo
  5. customthe residue purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-2f9edc565a494b239623315bc001e4a8
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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