Acetic Acid → HCID 9980908, compound

HRID 1725342Notes

Reaction equation

HRID 1725342 reaction equation
C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[C:10]2[C@H:17]1[O:21][C:20](=[O:22])[N:19]([CH2:23][CH2:24][CH2:25][NH:26][CH3:27])[CH2:18]1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[CH:37]=O.CC=C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[C:29]1[CH2:37][N:26]([CH3:27])[CH2:25][CH2:24][CH2:23][N:19]1[CH2:18][C@@H:17]([C:10]2[C:9]3[C:14](=[CH:15][CH:16]=[C:7]([O:6][CH3:5])[CH:8]=3)[N:13]=[CH:12][CH:11]=2)[O:21][C:20]1=[O:22]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 105532-Methyl-2-buteneHCID 96389Indole-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68839809HCID 68839809, compound

Product 1

HCID 9980908HCID 9980908, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Acetic acid (30 ul, 0.475 mmol) was added to a solution of (R)-5-(6-methoxy-quinolin-4-yl)-3-(3-methylamino-propyl)-oxazolidin-2-one (150 mg, 0.475 mmol) and 1H-indole-2-carbaldehyde [19005-93-7] (72 mg, 0.475 mmol) in methylene chloride stabilized over amylene (4.5 ml) and the mixture was stirred for 30 minutes. Sodium triacetoxyborohydride (230 mg, 1.01 mmol) was then added and stirring was maintained for 48 hours at room temperature. Then water (5 ml) was added, the organic phase was decanted, washed with water dried over magnesium sulfate and concentrated. The residue was chromatographed on silicagel eluting with methylene chloride-methanol (9-1) to give a first crop of pure (R)-3-{3-[(1H-indol-2-ylmethyl)-methyl-amino]-propyl}-5-(6-methoxy-quinolin-4-yl)-oxazolidin-2-one (18 mg) and a less pure fraction of 90 mg (estimated yield >50%).

Workup

  1. stirringstirring
  2. customthe organic phase was decanted
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silicagel
  7. washeluting with methylene chloride-methanol (9-1)

Sources & evidence

ORD record
ord-240b2077fbd54b7792b3c5e4b4eb6ee0
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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