Hydrochloric Acid → HCID 70022642, compound

HRID 1167458Notes

Reaction equation

HRID 1167458 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:4][CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:34].[Na+].Cl>CO.O>[NH2:34][C:2]1[CH:3]=[CH:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][O:20][C:21]4[CH:25]=[CH:24][O:23][N:22]=4)[O:16][C:15]3=[O:26])=[CH:10][C:9]=2[F:27])[CH2:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 69979965HCID 69979965, compound

Product 1

HCID 70022642HCID 70022642, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-(4-(4-Oxopiperidin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one (375 mg, 1 mmol) was dissolved in MeOH (10 ml), treated with ammonium acetate (771 mg, 10 mmol) and sodium cyanoborohydride (440 mg, 7 mmol) and refluxed 4 hours. The mixture was neutralised with 1 N hydrochloric acid, water (15 ml) added, and extracted with dichloromethane (3×15 ml), and dried (magnesium sulfate). Evaporation gave the desired product (334 mg).

Workup

  1. temperaturerefluxed 4 hours
  2. additionadded
  3. extractionextracted with dichloromethane (3×15 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customEvaporation

Sources & evidence

ORD record
ord-f8a38eff5a854cc5816dcadf3aa596e4
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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