Hydrochloric Acid → HCID 69458120, compound

HRID 1351964Notes

Reaction equation

HRID 1351964 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([C@H:14]([CH3:33])[CH2:15][C:16]3[C:24]4[C:19](=[C:20]([NH:25]C(=O)OC(C)(C)C)[CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl>CO>[NH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[NH:18][CH:17]=[C:16]2[CH2:15][C@H:14]([N:10]1[CH2:9][C@@H:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[O:12][C:11]1=[O:13])[CH3:33]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69458797HCID 69458797, compound

Product 1

HCID 69458120HCID 69458120, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of tert-butyl 3-((2R)-2-((5R)-5-(3-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl)propyl)-1H-indol-7-ylcarbamate (419.2 mg, 0.894 mmol) in methanol (2 mL) is added a 10% solution of hydrochloric acid in methanol (10 mL) under nitrogen atmosphere, and the mixture is stirred at room temperature for 21 hours. The solvent is evaporated, and the residue is separated into a saturated ammonia solution in chloroform and water, and the organic layer is washed with a saturated brine, and dried over anhydrous sodium sulfate. The solvent is evaporated, and the obtained crude product is purified by silica gel column chromatography (a saturated ammonia solution in chloroform-methanol=1:0 20:1) to give the title compound (299 mg, 90%).

Workup

  1. customThe solvent is evaporated
  2. customthe residue is separated into a saturated ammonia solution in chloroform and water
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is evaporated
  6. customthe obtained crude product
  7. customis purified by silica gel column chromatography (a saturated ammonia solution in chloroform-methanol=1:0 20:1)

Sources & evidence

ORD record
ord-6eebcda1781a430484f4a3a5903af440
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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