Ammonium fluoride → Ammonia

HRID 1866547Notes

Reaction equation

HRID 1866547 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:11]([NH:14][CH2:15][C@H:16]([O:26][Si](C(C)(C)C)(C)C)[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=2)([CH3:13])[CH3:12])[CH:5]=1.[F-].[NH4+]>CO.O>[NH3:14].[OH:26][C@H:16]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([CH2:24][OH:25])[CH:18]=1)[CH2:15][NH:14][C:11]([CH3:13])([CH3:12])[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([O:2][CH3:1])=[O:34]

Participants

6

Reactant 2

HCID 25516Ammonium fluorideHCID 690248003-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester

Product 2

HCID 222AmmoniaHCID 57978351Methyl 3-[2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)-2-methylpropyl]benzoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(2-[(2R)-2-(tert-butyldimethylsilanyloxy)-2-(4-hydroxy-3-hydroxymethyl-phenyl)ethylamino]-2-methylpropyl}benzoic acid methyl ester (preparation 36), (4.0 g, 8.21 mmol) and ammonium fluoride (3.04 g, 82.0 mmol) in methanol (20 mL) and water (5 mL) was heated at 40° C. for 18 hours. The reaction mixture was then concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol: 0.88 ammonia, 100:0:0 to 90:10:0.1, to afford the title compound as a white foam in 81% yield, 2.42 g.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was purified by column chromatography on silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-c8f3f9a5ee744094902ce3e0c28c9dd7
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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