2-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-(3-{methyl[(4-nitrophenyl)acetyl]amino}propyl)acetamide → 2-(4-Aminophenyl)-N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-N-methylacetamide

HRID 446549Notes

Reaction equation

HRID 446549 reaction equation
[F:1][C:2]([F:67])([F:66])[C:3]1[CH:4]=[C:5]([CH:59]=[C:60]([C:62]([F:65])([F:64])[F:63])[CH:61]=1)[C:6]([N:8]1[CH2:12][C@@:11]([CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][C:25]3([C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][C@@H:28]3[O:36][CH2:37][C:38]([N:40]([CH3:58])[CH2:41][CH2:42][CH2:43][N:44]([CH3:57])[C:45](=[O:56])[CH2:46][C:47]3[CH:52]=[CH:51][C:50]([N+:53]([O-])=O)=[CH:49][CH:48]=3)=[O:39])[CH2:24][CH2:23]2)([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:10][CH2:9]1)=[O:7]>C(O)C.[C].[Pd]>[NH2:53][C:50]1[CH:51]=[CH:52][C:47]([CH2:46][C:45]([N:44]([CH2:43][CH2:42][CH2:41][N:40]([C:38](=[O:39])[CH2:37][O:36][C@@H:28]2[C:25]3([CH2:24][CH2:23][N:22]([CH2:21][CH2:20][C@:11]4([C:13]5[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=5)[O:10][CH2:9][N:8]([C:6](=[O:7])[C:5]5[CH:4]=[C:3]([C:2]([F:1])([F:66])[F:67])[CH:61]=[C:60]([C:62]([F:64])([F:63])[F:65])[CH:59]=5)[CH2:12]4)[CH2:27][CH2:26]3)[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29]2)[CH3:58])[CH3:57])=[O:56])=[CH:48][CH:49]=1

Participants

4

Reactant 1

HCID 866634512-{[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}-N-methyl-N-(3-{methyl[(4-nitrophenyl)acetyl]amino}propyl)acetamide

Product 1

HCID 866634522-(4-Aminophenyl)-N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-N-methylacetamideYield 98%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

The compound (212 mg, 0.225 mmol) obtained in Example 57a was dissolved in ethanol (10 mL), 10% palladium-carbon (42 mg, 20% by weight) was added, and the mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. The reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:methanol, 10:1, v/v) to give the title compound (194 mg; yield, 98%) as a yellow oily substance.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-87669a72f7c74c21b3c761c37ffdce99
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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