Water → HCID 135434062, compound

HRID 601119Notes

Reaction equation

HRID 601119 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][N:12]=2)[C:7]([OH:14])=[C:6]([C:15]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17](=[O:26])(=[O:25])[N:16]=2)[C:5]1=[O:27])[CH:2]=[CH2:3].C[N+]1([O-])CC[O:32]CC1.C1COCC1.S(=O)(O)[O-].[Na+].[OH2:46]>[Os](=O)(=O)(=O)=O>[OH:46][CH:2]([CH2:3][OH:32])[CH2:1][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][N:12]=2)[C:7]([OH:14])=[C:6]([C:15]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[S:17](=[O:25])(=[O:26])[N:16]=2)[C:5]1=[O:27]

Participants

7

Reactant 5

HCID 962Water2×HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 136373785HCID 136373785, compound

Product 1

HCID 135434062HCID 135434062, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

The product of Example 55B (1.08 g, 0.028 mol) was reacted with osmium tetroxide (0.0007 mol) and N-methylmorpholine N-oxide (4.96 g, 0.043 mol) in a 1:1 mixture of water and THF (50 mL) at room temperature for 18 hours. The reaction mixture was treated with sodium bisulfite and diluted with water. The product precipitated from the aqueous mixture and was collected by vacuum filtration to give the title compound as a a white solid (1.09 g, 93%). MS (DCI/NH3) m/z 417 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 3.33 (m, 2H), 3.87 (m, 1H), 4.37 (m, 2H), 4.52 (t, J=6.07 Hz, 1H), 4.78 (d, J=5.52 Hz, 1H), 7.17 (dd, J=7.72, 4.78 Hz, 1H), 7.29 (m, 2H), 7.56 (m, 1H), 7.67 (d, J=6.99 Hz, 1H), 8.40 (dd, J=7.72, 1.84 Hz, 1H), 8.53 (dd, J=4.78, 1.84 Hz, 1H), 15.80 (m, 1H).

Workup

  1. customThe product precipitated from the aqueous mixture
  2. filtrationwas collected by vacuum filtration

Sources & evidence

ORD record
ord-fcb3eac8a5a244898b0369f5a6e8b330
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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