Triacetoxyperiodinane → HCID 18465818, compound

HRID 2230445Notes

Reaction equation

HRID 2230445 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=[O:3].[C:23]([NH:31][CH:32]1[C:38](=[O:39])[N:37]2[CH:40]([C:44]([NH:46][CH:47]([CH:56]([OH:68])[CH2:57][O:58][CH2:59][C:60]3[C:65]([Cl:66])=[CH:64][CH:63]=[CH:62][C:61]=3[Cl:67])[CH2:48][C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:45])[CH2:41][CH2:42][CH2:43][N:36]2[C:35](=[O:69])[CH2:34][CH2:33]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl.CCOC(C)=O>[C:23]([NH:31][CH:32]1[C:38](=[O:39])[N:37]2[CH:40]([C:44]([NH:46][CH:47]([C:56](=[O:68])[CH2:57][O:58][C:59](=[O:3])[C:60]3[C:65]([Cl:66])=[CH:64][CH:63]=[CH:62][C:61]=3[Cl:67])[CH2:48][C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])=[O:45])[CH2:41][CH2:42][CH2:43][N:36]2[C:35](=[O:69])[CH2:34][CH2:33]1)(=[O:30])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 54324685HCID 54324685, compound

Product 1

HCID 18465818HCID 18465818, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin reagent (3.82 g; 9.0 mmol) was added to a stirred solution of the alcohol 215e (3.17 g; 4.5 mmol) in CH2Cl2 (100 ml). The mixture was sirred for 1 h, diluted with EtOAc (300 ml), then washed with a 1:1 mixture of sat. Na2S2O3 and sat. NaHCO3 (100 ml) followed by brine (100 ml). The mixture was dried (MgSO4) then concentrated. The residue was purified by flash chromatography to afford 2.2 g (70%) of 216e as a colourless solid: mp 102-107° C.; [α]D32 −82.5 (c 0.1, CH2Cl2); IR (KBr) 3374, 2937, 1739, 1661, 1525, 1433, 1275, 1260, 1152; 1H NMR (CDCl3) δ7.85-7.78 (2H, m), 7.57-7.32 (6H, m), 7.09 (1H, d, J=7.9), 7.01 (1H, d, J 7.3), 5.25-5.16 (1H, m), 5.16-5.05 (1H, m), 5.15 (1H, d), 5.03 (1H, d), 4.99-4.90 (1H, m), 4.68-4.54 (1H, m), 3.31-3.17 (1H, m), 3.17-2.72 (4H, m), 2.45-2.35 (1H, m), 2.30-1.66 (5H, m), 1.44 (9H, s); Anal. Calcd for C33H36Cl2N4O9.0.5H2O: C, 55.62; H, 5.23; N, 7.86; Cl, 9.95. Found: C, 55.79; H, 5.15; N, 7.80; Cl 9.81. MS (ES+) 729/7/5 (M+Na), 707/5/3 (M+1), 163 (100%).

Workup

  1. washwashed with a 1:1 mixture of sat. Na2S2O3 and sat. NaHCO3 (100 ml)
  2. dry with materialThe mixture was dried (MgSO4)
  3. concentrationthen concentrated
  4. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a767dcdbe12a46f4a4c879899668ba05
Source dataset
uspto-grants-2002_07
Patent number
US06423840B1

Reaction notes

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