N-(4-Methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamide → 5-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamide

HRID 909660Notes

Reaction equation

HRID 909660 reaction equation
COC1C=CC([CH2:7][N:8](C)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[C:23]([C:25]4[NH:26][C:27]([C:30]5[O:31][C@@H:32]([CH3:35])[CH2:33][N:34]=5)=[CH:28][CH:29]=4)[CH:22]=[C:21]([O:36][C@@H:37]([CH3:41])[CH2:38][O:39][CH3:40])[CH:20]=3)=[CH:14][N:13]=2)(=[O:11])=[O:10])=CC=1>FC(F)(F)C(O)=O>[CH3:40][O:39][CH2:38][C@H:37]([CH3:41])[O:36][C:21]1[CH:20]=[C:19]([CH:24]=[C:23]([C:25]2[NH:26][C:27]([C:30]3[O:31][C@@H:32]([CH3:35])[CH2:33][N:34]=3)=[CH:28][CH:29]=2)[CH:22]=1)[O:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][CH3:7])(=[O:11])=[O:10])=[N:13][CH:14]=1

Participants

3

Reactant 1

HCID 66681054N-(4-Methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamide

Product 1

HCID 666832525-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamideYield 88.4%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(4-Methoxybenzyl)-5-(3-[(1S)-2-methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)-N-methylpyridine-2-sulfonamide (292 mg, 0.47 mmol) synthesized in Example (121c) was dissolved in trifluoroacetic acid (2 mL), and stirring was carried out at 45° C. for 1 hour. The solvent was distilled off under reduced pressure, methylene chloride and triethylamine were added in small portions to the residue, and the solvent was distilled off again under reduced pressure. The resulting residue was purified using silica gel column chromatography (elution solvent: methanol/methylene chloride=0%-4%) to afford the desired compound (208 mg, yield 88%) as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, methylene chloride and triethylamine
  2. additionwere added in small portions to the residue
  3. distillationthe solvent was distilled off again under reduced pressure
  4. customThe resulting residue was purified
  5. washsilica gel column chromatography (elution solvent: methanol/methylene chloride=0%-4%)

Sources & evidence

ORD record
ord-b5613874dde34524a2b54508b4459d8e
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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