Acetic Acid → Ammonia

HRID 916056Notes

Reaction equation

HRID 916056 reaction equation
[Si]([O:8][C@H:9]([C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=1)[CH2:10][NH:11][C@H:12]([CH3:35])[CH2:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([NH:23][CH2:24][C:25]2[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=2[O:33][CH3:34])=[O:22])[CH:17]=[CH:18][CH:19]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].[NH4+]>CO>[NH3:11].[CH3:34][O:33][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:25]=1[CH2:24][NH:23][C:21](=[O:22])[CH2:20][C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([CH2:13][C@H:12]([NH:11][CH2:10][C@H:9]([OH:8])[C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]([CH2:43][OH:44])[CH:37]=2)[CH3:35])[CH:15]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 25516Ammonium fluorideHCID 12149178HCID 12149178, compound

Product 2

HCID 222AmmoniaHCID 11409594HCID 11409594, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2-(3-{(2R)-2-[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-hydroxy-3-hydroxymethyl-phenyl)-ethylamino]-propyl}-phenyl)-N-(2,6-dimethoxybenzyl)-acetamide (Preparation 1) (125 mg, 0.20 mmol) in methanol (6 ml) was treated with acetic acid (6 ml) and ammonium fluoride (74 mg, 2.0 mmol) and the reaction heated to 40° C. for 16 hours. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95:5:0.5 changing to 93:7:0.7, by volume) to give the title compound as a white solid after trituration with diethyl ether (59 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b7d2f00f1fea4c928a8e0b2b95f4ae13
Source dataset
uspto-grants-2007_09
Patent number
US07268147B2

Reaction notes

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