Tetrahydrofuran → 3-((3',4'-Dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl)methyl)-N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

HRID 920232Notes

Reaction equation

HRID 920232 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]([C:21]1[S:25][N:24]=[CH:23][N:22]=1)[S:7]([C:10]1[C:19]([F:20])=[CH:18][C:13]2[NH:14][C:15](=[O:17])[O:16][C:12]=2[CH:11]=1)(=[O:9])=[O:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:51]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][C:59]=2[CH2:61]O)[CH2:54][CH2:53][C:52]21[O:66][CH2:65][CH2:64][O:63]2.C1COCC1>C(Cl)Cl.CCOC(C)=O>[CH2:51]1[C:60]2[C:55](=[CH:56][CH:57]=[CH:58][C:59]=2[CH2:61][N:14]2[C:13]3[CH:18]=[C:19]([F:20])[C:10]([S:7]([N:6]([CH2:5][C:4]4[CH:26]=[CH:27][C:28]([O:30][CH3:31])=[CH:29][C:3]=4[O:2][CH3:1])[C:21]4[S:25][N:24]=[CH:23][N:22]=4)(=[O:8])=[O:9])=[CH:11][C:12]=3[O:16][C:15]2=[O:17])[CH2:54][CH2:53][C:52]21[O:63][CH2:64][CH2:65][O:66]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 89525954N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamideHCID 89533747(3',4'-Dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl)methanol

Product 1

HCID 895263363-((3',4'-Dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-8'-yl)methyl)-N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

To a flask containing N-(2,4-Dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide (11-3) (2.13 g, 4.57 mmol), resin bound (PS) TRIPHENYLPHOSPHINE (5.27 g, 9.70 mmol) & DTBAD (2.187 g, 9.50 mmol) & (3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalen]-8′-yl)methanol (19-3) (1.162 g, 5.28 mmol) was added anhydrous THF (40 ml). The reaction mixture was then capped (not under N2) & stirred at room temperature for ˜16 hours (overnight). Followed by LC/MS. The reaction mixture was diluted with DCM/EtOAc, filtered (to remove the resin), it was noticed that the filtrate was cloudy white so it was filtered to yield 3-((3′,4′-dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalen]-8′-yl)methyl)-N-(2,4-dimethoxybenzyl)-5-fluoro-2-oxo-N-(1,2,4-thiadiazol-5-yl)-2,3-dihydrobenzo[d]oxazole-6-sulfonamide (19-4).

Workup

  1. customThe reaction mixture was then capped (not under N2) &
  2. filtrationfiltered (
  3. customto remove the resin), it
  4. filtrationwas filtered

Sources & evidence

ORD record
ord-1e9f20aa31a64877835a07acc3a270d6
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

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