N,N-Bis(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)pyridine-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)pyridine-2-sulfonamide

HRID 909657Notes

Reaction equation

HRID 909657 reaction equation
COC1C=CC(C[N:8](CC2C=CC(OC)=CC=2)[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]([NH2:8])(=[O:10])=[O:11])=[N:13][CH:14]=1

Participants

3

Reactant 1

HCID 66681273N,N-Bis(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)pyridine-2-sulfonamide

Product 1

HCID 580654765-(3-[(1S)-2-Methoxy-1-methylethoxy]-5-{5-[(5S)-5-methyl-4,5-dihydro-1,3-oxazol-2-yl]-1H-pyrrol-2-yl}phenoxy)pyridine-2-sulfonamideYield 99%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N,N-Bis(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)pyridine-2-sulfonamide (160 mg, 0.24 mmol) synthesized in Example (120c) was dissolved in trifluoroacetic acid (2 mL), and stirring was carried out at 40° C. for 8 hours. 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%-5%) to afford the desired compound (106 mg, yield 99%) 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%-5%)

Sources & evidence

ORD record
ord-d4b77c6a216e456295f1770c37b2d148
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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