Potassium Carbonate → HCID 66956709, compound

HRID 2066664Notes

Reaction equation

HRID 2066664 reaction equation
C([O:4][CH2:5][C@@:6]1([CH3:18])[O:11][C:10]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:9]2[CH2:8][CH2:7]1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.O>[CH3:18][C@:6]1([CH2:5][OH:4])[O:11][C:10]2=[N:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][N:9]2[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66956582HCID 66956582, compound

Product 1

HCID 66956709HCID 66956709, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Hydrolysis of (S)-acetate 161 (426 mg, 1.67 mmol) with K2CO3 in MeOH/water as in Example 2EEE above, followed by chromatography of the product on silica gel, eluting with 0-1% MeOH/CH2Cl2 (forerun), and then with 1-2.5% MeOH/CH2Cl2, gave [(7S)-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-yl]methanol (162) (343 mg, 96%) as a pale yellow solid that was used directly in the next step; 1H NMR [(CD3)2SO] δ 8.03 (s, 1H), 5.22 (br t, J=5.7 Hz, 1H), 4.13 (dt, J=13.0, 6.0 Hz, 1H), 4.05 (ddd, J=12.9, 8.1, 5.6 Hz, 1H), 3.54 (dd, J=11.6, 5.4 Hz, 1H), 3.48 (dd, J=11.6, 5.7 Hz, 1H), 2.21 (ddd, J=14.4, 8.1, 5.9 Hz, 1H), 2.00 (dt, J=14.4, 5.8 Hz, 1H), 1.32 (s, 3H); [α]D27 18.0° (c 1.00, DMF).

Workup

  1. washeluting with 0-1% MeOH/CH2Cl2 (forerun)

Sources & evidence

ORD record
ord-028fad9b3fa34df89f0c3301508d3b76
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

Loading…