HCID 86613447, compound → HCID 67278875, compound

HRID 2387576Notes

Reaction equation

HRID 2387576 reaction equation
[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:73]=[CH:72][C:15]([O:16][CH2:17][C:18]3([O:42][C:43](=[O:71])[CH:44]([NH:60]C(OCC4C=CC=CC=4)=O)[CH2:45][CH2:46][CH2:47][CH2:48][NH:49]C(OCC4C=CC=CC=4)=O)[CH2:23][CH2:22][N:21]([C:24]4[N:33]=[C:32]5[C:27]([C:28](=[O:40])[C:29]([C:37]([OH:39])=[O:38])=[CH:30][N:31]5[CH:34]5[CH2:36][CH2:35]5)=[CH:26][C:25]=4[F:41])[CH2:20][CH2:19]3)=[C:14]([F:74])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]>[OH-].[Pd+2].[OH-]>[C:1]([NH:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:73]=[CH:72][C:15]([O:16][CH2:17][C:18]3([O:42][C:43](=[O:71])[CH:44]([NH2:60])[CH2:45][CH2:46][CH2:47][CH2:48][NH2:49])[CH2:19][CH2:20][N:21]([C:24]4[N:33]=[C:32]5[C:27]([C:28](=[O:40])[C:29]([C:37]([OH:39])=[O:38])=[CH:30][N:31]5[CH:34]5[CH2:36][CH2:35]5)=[CH:26][C:25]=4[F:41])[CH2:22][CH2:23]3)=[C:14]([F:74])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86613447HCID 86613447, compound

Product 1

HCID 67278875HCID 67278875, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

A suspension of 94 mg 7-[4-{4-[(5S)-5-(acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-(2,6-bis-benzyloxycarbonylamino-hexanoyloxy)-piperidin-1-yl]-1-cyclo-propyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid (MW: 1024.05, 0.091 mmol) and 20 mg of palladium hydroxide 20% on activated carbon in 20 ml of a 6/3/1 dichloromethane/methanol/water mixture was stirred at room temperature under hydrogen for four hours. The catalyst was filtered off using a glass fibre filter paper. The solvents were evaporated under reduced pressure and the residue dissolved in 10 ml methanol. The solution was diluted with 20 ml water while a white solid precipitated. The solid was collected and dried. Yield: 29 mg, 43%. MS: 757.0 (M+H)+, 755.2 Method ESI+, ESI−.

Workup

  1. filtrationThe catalyst was filtered off
  2. filtrationfilter paper
  3. customThe solvents were evaporated under reduced pressure
  4. dissolutionthe residue dissolved in 10 ml methanol
  5. additionThe solution was diluted with 20 ml water while a white solid
  6. customprecipitated
  7. customThe solid was collected
  8. customdried

Sources & evidence

ORD record
ord-338c58dbb2d54343b985aa0c3996d223
Source dataset
uspto-grants-2012_09
Patent number
US08268812B2

Reaction notes

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