Water → HCID 19771723, compound

HRID 1614594Notes

Reaction equation

HRID 1614594 reaction equation
C1C=C([O:7]O)C(C(O)=O)=C(C(O)=O)C=1.[CH2:15]([C:17]1[N:22]=[C:21]2[CH2:23][CH2:24][S:25][CH2:26][C:20]2=[C:19]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]3[N:42]=[N:43][N:44]([C:46]([C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)([C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[N:45]=3)=[CH:31][CH:30]=2)[CH:18]=1)[CH3:16].[OH2:65]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[CH2:15]([C:17]1[N:22]=[C:21]2[CH2:23][CH2:24][S:25](=[O:7])(=[O:65])[CH2:26][C:20]2=[C:19]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:41]3[N:42]=[N:43][N:44]([C:46]([C:53]4[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=4)([C:47]4[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=4)[C:59]4[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=4)[N:45]=3)=[CH:33][CH:34]=2)[CH:18]=1)[CH3:16]

Participants

6

Reactant 3

HCID 962Water2×HCID 19771696HCID 19771696, compoundHCID 198097063-Hydroperoxyphthalic acid2×

Product 1

HCID 19771723HCID 19771723, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Monoperoxyphthalic acid, magnesium salt hexahydrate (1.38 g) was added to a mixture of 7,8-dihydro-2-ethyl-4-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methoxy]-5H-thiopyrano[4,3-b]pyridine (1.5 g) and benzyltriethylammonium chloride (0.3 g) in dichloromethane (50 ml) and water (20 ml). The mixture was stirred for 4 hours and then a further quantity of monoperoxyphthalic acid, magnesium salt hexahydrate (138 mg) was added. Stirring was continued for 1 hour and then the mixture was diluted with dichloromethane (100 ml) and water (100 ml). The organic layer was separated and dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by flash chromtography, eluting with methanol/dichlormethane (1.49 v/v) to give 7,8-dihydro-2-ethyl-4-[(2'-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4yl)methoxy]-5H-thiopyrano[4,3b]pyridine S,S-dioxide (A) (320 mg), as a foam; NMR (CDCl3); 1.3(t, 3H), 2,75(q, 2H), 3.35(t, 2H), 3.55(t, 2H), 4.15(s, 2H), 5.0(s, 2H), 6.65(s, 1H), 6.9-7.0(m, 6H), 7.1-7.5(m, 16H), 7.95-8.0(m, 1H).

Workup

  1. stirringStirring
  2. waitwas continued for 1 hour
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed by evaporation
  6. customThe residue was purified by flash chromtography
  7. washeluting with methanol/dichlormethane (1.49 v/v)

Sources & evidence

ORD record
ord-bdf121fff03b40cf8942936f54141d52
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

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