Triacetoxyperiodinane → HCID 23648430, compound

HRID 1182283Notes

Reaction equation

HRID 1182283 reaction equation
[OH:1][C@@H:2]([CH2:30][NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)(=[O:34])=[O:33])[C@@H:3]([NH:5][C:6](=[O:29])[O:7][C@H:8]([CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)=[N:15]1)[C:9]([CH3:12])([CH3:11])[CH3:10])[CH3:4].O[C@H](CNS(C1C=CC=CN=1)(=O)=O)[C@@H](NC(=O)O[C@H](CN1C=CC(C2C=CC(C(F)(F)F)=CC=2)=N1)C(C)(C)C)C.C(=O)(O)[O-].[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:4][C@H:3]([NH:5][C:6](=[O:29])[O:7][C@H:8]([CH2:13][N:14]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:28])[F:27])=[CH:21][CH:20]=2)=[N:15]1)[C:9]([CH3:11])([CH3:10])[CH3:12])[C:2](=[O:1])[CH2:30][NH:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)(=[O:34])=[O:33]

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 71164600HCID 71164600, compoundHCID 71164601HCID 71164601, compound

Product 1

HCID 23648430HCID 23648430, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.130 g (0.22 mmol) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S,2S)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate & (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl (1S,2R)-2-hydroxy-1-methyl-3-[(2-pyridinylsulfonyl)amino]propylcarbamate in 2.0 mL of dichloromethane was added 0.020 g (0.24 mmol) of sodium bicarbonate and 0.11 g (0.26 mmol) of Dess-Martin periodinane. The reaction mixture was stirred for 15 min and then purified via silica gel chromatography eluting with ethyl acetate:hexane (7:3) to afford 0.078 g (59%) of (1S)-2,2-dimethyl-1-({3-[4-(trifluoromethyl)phenyl]-1H-pyrazol-1-yl}methyl)propyl(1S)-1-methyl-2-oxo-3-[(2-pyridinylsulfonyl)amino]propylcarbamate as a colorless oil. 1H-NMR (300 MHz, CDCl3) δ 8.58 (m, 1H), 7.98–7.89 (m, 4H), 7.63 (m, 2H), 7.46 (m, 2H), 6.65 (s, 1H), 5.56 (m, 1H), 1.05 (s, 9H), 5.24 (d, J=7 Hz, 1H), 4.98 (m, 1H), 4.44 (m, 1H), 4.34–4.12 (m, 4H), 1.12 (d, J=7 Hz, 3H); LC-MS m/z 582 (M+H).

Workup

  1. custompurified via silica gel chromatography
  2. washeluting with ethyl acetate:hexane (7:3)

Sources & evidence

ORD record
ord-c48797e2f08d4581b0327fa954dd75b9
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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