Hydrochloric Acid → 6-(N-((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-iodo-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

HRID 2190201Notes

Reaction equation

HRID 2190201 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:15]([C:16]([NH:18][CH3:19])=[O:17])=[C:14]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[O:13][C:5]2=[N:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[CH2:27]([C@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[C@@H:41]([CH3:46])[CH2:42][CH2:43][CH2:44]Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Na+].[I-].Cl>CC(N(C)C)=O>[CH2:27]([C@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:47])[C@@H:41]([CH3:46])[CH2:42][CH2:43][CH2:44][N:8]([C:7]1[N:6]=[C:5]2[O:13][C:14]([C:20]3[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=3)=[C:15]([C:16]([NH:18][CH3:19])=[O:17])[C:4]2=[CH:3][C:2]=1[I:1])[S:9]([CH3:12])(=[O:10])=[O:11])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 11210408(S)-4-benzyl-3-((S)-5-bromo-2-methylpentanoyl)oxazolidin-2-oneHCID 580523565-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

Product 1

HCID 580525336-(N-((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-iodo-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

To 5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (1 g, 2.061 mmol) was added (S)-4-benzyl-3-((S)-5-bromo-2-methylpentanoyl)oxazolidin-2-one (0.730 g, 2.061 mmol) and CESIUM CARBONATE (2.014 g, 6.18 mmol) and NaI (0.309 g, 2.061 mmol) and DMA (4.12 mL). Heated 100° C. 2 hr (note: done at 1 hr) Added 30 mL 1N HCl and extracted with EtOAc, washed with brine, and conc. on vac. 3.05 g crude brown oil. Taken up in minimum EtOAc 30 mL and triturated into a stirring solution of 200 mL heptanes. to give a white solid which is filtered. Purified on 120 g Silica: 0-20% DCM/ether 15 column volumes 964 mg 6-(N—((S)-5-((S)-4-benzyl-2-oxooxazolidin-3-yl)-4-methyl-5-oxopentyl)methylsulfonamido)-5-iodo-N-methyl-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. customtriturated into a stirring solution of 200 mL heptanes
  4. customto give a white solid which
  5. filtrationis filtered
  6. customPurified on 120 g Silica

Sources & evidence

ORD record
ord-b82da87c2c894042930a7c1d9fc7a07a
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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