Lithium Hydroxide → HCID 71288128, compound

HRID 1497901Notes

Reaction equation

HRID 1497901 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[C:13](OCC(O)=O)(=[O:15])[CH3:14].[OH:21]/[N:22]=[C:23](/[C:25]1[CH:26]=[CH:27][C:28]([CH3:39])=[C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH:30]=1)\[NH2:24].[Li+].[OH-].C([O-])(O)=O.[Na+]>CN1C(=O)CCC1.C1COCC1.CO.O>[OH:15][CH2:13][C:14]1[O:21][N:22]=[C:23]([C:25]2[CH:26]=[CH:27][C:28]([CH3:39])=[C:29]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:35])([CH3:36])[CH3:37])[CH:30]=2)[N:24]=1

Participants

8

Reactant 5

HCID 3939Lithium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 83766Acetoxyacetic acidHCID 516892Sodium BicarbonateHCID 62666076HCID 62666076, compound

Product 1

HCID 71288128HCID 71288128, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

CDI (1.76 g, 10.78 mmol) was added portion-wise to a stirred solution of 2-acetoxyacetic acid (1.27 g, 10.78 mmol) in NMP (5 mL). After 10 minutes, (Z)-tert-butyl 5-(N′-hydroxycarbamimidoyl)-2-methylphenylcarbamate (35) (1.43 g, 5.39 mmol) was added in one portion and stirred for another hour at room temperature. The solution was then heated via microwave at 125° C. for 15 minutes. The solution was partitioned with EtOAc and water. The organic phase was separated, dried over Na2SO4 and concentrated to give a residue which was dissolved in THF/MeOH/H2O (3:2:1, 5 mL) and followed by addition of 6N LiOH (5.4 mL). The resulting mixture was stirred for 10 minutes. Then aqueous 2M NaHCO3 (30 mL) was added and the solution was extracted with EtOAc. The organic layers were dried over Na2SO4 and concentrated to give a residue which was purified over silica gel to afford tert-butyl (5-(5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)carbamate (137). MS m/z 306.0 (M+1)+.

Workup

  1. temperatureThe solution was then heated via microwave at 125° C. for 15 minutes
  2. customThe solution was partitioned with EtOAc and water
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a residue which
  7. stirringThe resulting mixture was stirred for 10 minutes
  8. extractionthe solution was extracted with EtOAc
  9. dry with materialThe organic layers were dried over Na2SO4
  10. concentrationconcentrated
  11. customto give a residue which
  12. customwas purified over silica gel

Sources & evidence

ORD record
ord-a1b2177f52d1402685c24078a95a7691
Source dataset
uspto-grants-2015_12
Patent number
US09199981B2

Reaction notes

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