Isopropanol → HCID 86745097, compound

HRID 728887Notes

Reaction equation

HRID 728887 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C@H:8]([CH:11]=[C:12]([CH3:24])[CH2:13][P:14]([O:20][CH:21]([CH3:23])[CH3:22])([O:16][CH:17]([CH3:19])[CH3:18])=[O:15])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C([OH:29])(C)C.[Na]>CC(C)=O.[O-2].[Cr+6].[O-2].[O-2].S(=O)(=O)(O)O>[C:1]([O:5][C:6]([NH:7][C@H:8]([CH:11]=[C:12]([CH3:24])[CH2:13][P:14]([O:16][CH:17]([CH3:18])[CH3:19])([O:20][CH:21]([CH3:23])[CH3:22])=[O:15])[C:9]([OH:29])=[O:10])=[O:25])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 3776IsopropanolHCID 5360545SodiumHCID 53861343HCID 53861343, compound

Product 1

HCID 86745097HCID 86745097, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolventHCID 10219390chromium (VI) trioxideSolvent

Procedure

To a solution of 1.6 g of alcohol 2 according to b) in 60 ml of acetone there are added at 0°-5° 3.3 ml of a solution that is 3.25 molar in chromium(VI) oxide and 5.29 molar in sulphuric acid. The mixture is stirred at 0° for 6 hours and at room temperature for 12 hours. After the addition of 5 ml of isopropanol and 40 ml of 20% sodium chloridesolution, the mixture is stirred for 10 minutes and is then extracted continuously with methyl acetate for 15 hours in a Kutscher-Steudel apparatus. The organic phase is dried over sodium sulphate and concentrated by evaporation, and the residue is chromatographed on 75 g ofsilica gel with hexane/ethyl acetate/acetic acid 16:10:1. This yields 0.92 g of 3, [α]D =-94.5° (c=1.2, CHCl3). 1H-NMR (300 MHz, CDCl3): 1.2-1.3 (4d, (2-propo)2); 1.4 (s, (CH3)3CO); 1.95 (d, J=3, CH3 --C(4)); 3.5 and 3.62 (2 d×d, J=23 and 15, 2H--C(5)); 4.66 (m, (2-propo)2); 4.92 (m, H--C(2)); 5.30 (m, H--C(3)); 5.42 (d, J=7, NH); 9.0-10.0 (broad, CO2H).

Workup

  1. stirringthe mixture is stirred for 10 minutes
  2. extractionis then extracted continuously with methyl acetate for 15 hours in a Kutscher-Steudel apparatus
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. concentrationconcentrated by evaporation
  5. customthe residue is chromatographed on 75 g ofsilica gel with hexane/ethyl acetate/acetic acid 16:10:1
  6. customThis yields 0.92 g of 3, [α]D =-94.5° (c=1.2, CHCl3)
  7. custom3.5 and 3.62 (2 d×d, J=23 and 15, 2H--C(5))

Sources & evidence

ORD record
ord-293d7aeff40646caa25457def283e0e2
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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