Potassium Carbonate → HCID 178452937, compound

HRID 1879579Notes

Reaction equation

HRID 1879579 reaction equation
[N:1]1[N:2]=[C:3]([SH:6])[NH:4][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]([C@:24]1([NH:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:29][C@H:28](OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:27]2[C@H:25]1[C@H:26]2[C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[F:51])=[O:42])=[O:23]>CN(C)C=O>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][O:21][C:22]([C@:24]1([NH:52][C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:29][C@@H:28]([S:6][C:3]2[NH:4][CH:5]=[N:1][N:2]=2)[C@@H:27]2[C@H:25]1[C@H:26]2[C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[F:51])=[O:42])=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 87320350bis[(2-fluorophenyl)methyl] (1S,2S,4S,5R,6R)-2-(tert-butoxy carbonylamino)-4-(p-tolylsulfonyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylateHCID 178527972HCID 178527972, compound

Product 1

HCID 178452937HCID 178452937, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Add 4H-1,2,4-triazole-3-thiol (0.59 g, 5.87 mmol) and potassium carbonate (0.81 g, 5.87 mmol) to a solution of bis[(2-fluorophenyl)methyl](1S,2S,4S,5R,6R)-2-(tert-butoxy carbonylamino)-4-(p-tolylsulfonyloxy)bicyclo[3.1.0]hexane-2,6-dicarboxylate (2.63 g, 3.92 mmol) in dry N,N-dimethylformamide (15.66 mL). Heat the resulting mixture at 70° C. under nitrogen in a sealed tube and maintain stirring overnight. Quench with water and dilute with ethyl acetate. Wash the organic layer with citric acid solution (10% in water), brine. Dry over sodium sulfate, filter and concentrate to give the crude material as a pale brown oil (2.3 g). Purify by flash chromatography eluting with ethyl acetate:hexane (30:70 to 70:30) to give the title product as a colorless oil (1.84 g, 3.06 mmol). MS (m/z): 601 (M+1), 623 (M+23).

Workup

  1. temperaturemaintain
  2. customQuench with water
  3. additiondilute with ethyl acetate
  4. washWash the organic layer with citric acid solution (10% in water), brine
  5. dry with materialDry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto give the crude material as a pale brown oil (2.3 g)
  9. customPurify by flash chromatography
  10. washeluting with ethyl acetate:hexane (30:70 to 70:30)

Sources & evidence

ORD record
ord-61d00e79d4984c8abfc96e27d703ebea
Source dataset
uspto-grants-2012_11
Patent number
US08318184B2

Reaction notes

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