tert-Butanol → HCID 69458797, compound

HRID 1351963Notes

Reaction equation

HRID 1351963 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]([CH3:28])[CH2:15][C:16]3[C:24]4[C:19](=[C:20](C(O)=O)[CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[Cl-].[NH4+].[C:55]([OH:59])([CH3:58])([CH3:57])[CH3:56]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]2[O:12][C:11](=[O:13])[N:10]([C@H:14]([CH3:28])[CH2:15][C:16]3[C:24]4[C:19](=[C:20]([NH:48][C:51](=[O:36])[O:59][C:55]([CH3:58])([CH3:57])[CH3:56])[CH:21]=[CH:22][CH:23]=4)[NH:18][CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 199401P,P-Diphenylphosphinic azideHCID 69458599HCID 69458599, compound

Product 1

HCID 69458797HCID 69458797, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-{(2R)-2-[(5R)-5-(3-chlorophenyl)-2-oxo-1,3-oxazolidin-3-yl]propyl}-1H-indole-7-carboxylic acid (504 mg, 1.26 mmol) in toluene (25 mL) and t-butyl alcohol (12.5 mL) are added diphenyl-phosphoryl azide (379 μL, 1.76 mmol) and triethylamine (245 μL, 1.76 mmol) under nitrogen atmosphere, and the mixture is stirred at room temperature for 30 minutes, and further stirred at 100° C. for 5 hours. The reaction solution is poured into a saturated aqueous ammonium chloride solution, and the mixture is extracted with ethyl acetate. 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 (n-hexane:ethyl acetate=2:1→1:1) to give the title compound (427 mg, 72%).

Workup

  1. stirringfurther stirred at 100° C. for 5 hours
  2. extractionthe mixture is extracted with ethyl acetate
  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 (n-hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-01ae5de52fed4a508285d4def8bb0660
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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