Hydrochloric Acid → HCID 66956706, compound

HRID 2066662Notes

Reaction equation

HRID 2066662 reaction equation
O.C([O:5][CH2:6][C@:7]1([CH3:19])[O:12][C:11]2=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]2[CH2:9][CH2:8]1)(=O)C.C([O-])([O-])=O.[K+].[K+].Cl>CO>[CH3:19][C@@:7]1([CH2:6][OH:5])[O:12][C:11]2=[N:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][N:10]2[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 66956584[(7R)-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-yl]methyl acetate

Product 1

HCID 66956706HCID 66956706, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Water (4 mL) was added dropwise to a stirred mixture of (R)-acetate 158 (427 mg, 1.67 mmol) and K2CO3 (256 mg, 1.85 mmol) in MeOH (36 mL). After stirring at room temperature for 4 h, the mixture was cooled in ice and treated with 0.1M HCl (37 mL, 3.70 mmol). The solvents were removed under reduced pressure and the residue was chromatographed on silica gel. Elution with 0-1% MeOH/CH2Cl2 firstly gave foreruns, and then further elution with 1-2.5% MeOH/CH2Cl2 gave [(7R)-7-methyl-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-yl]methanol (159) (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), 5.23 (br t, J=5.4 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, 4.9 Hz, 1H), 3.48 (dd, J=11.6, 5.2 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]D27−16.0° (c 1.00, DMF).

Workup

  1. temperaturethe mixture was cooled in ice
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was chromatographed on silica gel
  4. washElution with 0-1% MeOH/CH2Cl2 firstly gave foreruns
  5. washfurther elution with 1-2.5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-aff30d3c674049548f79dfe21e1c85ce
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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