Ammonium formate → HCID 69025804, compound

HRID 1866552Notes

Reaction equation

HRID 1866552 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13](=[O:53])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][C:23]([NH:26][CH2:27][CH:28]([C:37]2[CH:42]=[CH:41][C:40]([O:43]CC3C=CC=CC=3)=[C:39]([CH2:51][OH:52])[CH:38]=2)[O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])([CH3:25])[CH3:24])[CH:17]=1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[Si:30]([O:29][C@H:28]([C:37]1[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([CH2:51][OH:52])[CH:38]=1)[CH2:27][NH:26][C:23]([CH3:25])([CH3:24])[CH2:22][C:18]1[CH:17]=[C:16]([CH2:15][CH2:14][C:13]([OH:53])=[O:12])[CH:21]=[CH:20][CH:19]=1)([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:32])[CH3:31]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69024988HCID 69024988, compound

Product 1

HCID 69025804HCID 69025804, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Ammonium formate (139 mg, 2.20 mmol) and palladium (II) hydroxide (50 mg) was added to a solution of 3-(3-{2-[2-(4-benzyloxy-3-hydroxymethyl-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)ethylamino]-2-methyl-propyl}-phenyl)-acrylic acid benzyl ester (preparation 143), (300 mg, 0.44 mmol) in ethanol (10 mL) and the mixture was heated under reflux for 30 minutes. The reaction mixture was then cooled, filtered through Arbocel® and concentrated in vacuo to afford the title compound in 90% yield, 200 mg. 1H NMR (400 MHz, CD3OD) δ: 7.30 (1H, s), 7.20 (1H, m), 7.18 (1H, d), 7.09 (2H, m), 7.00 (1H, d), 6.78 (1H, d), 4.88 (1H, m), 4.63 (2H, m), 3.11 (2H, m), 2.83 (4H, m), 2.48 (2H, m), 1.23 (6H, s), 0.81 (9H, s), −0.03 (3H, s), −0.18 (3H, s) ppm; LRMS ESI m/z 502 [M+H]+

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered through Arbocel®
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-baafb3c901114827aefa0495a2ba2a1a
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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