Methanol → HCID 68440920, compound

HRID 1455555Notes

Reaction equation

HRID 1455555 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:24][CH:23]2[C:25](=[C:26]([C:28](O)=[O:29])[F:27])[CH:19]([CH2:20][CH2:21][CH2:22]2)[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].[Cl:31][C:32]1[S:33][C:34]([Cl:42])=[C:35]([Cl:41])[C:36]=1[S:37]([NH-:40])(=[O:39])=[O:38].CO>CN(C1C=CN=CC=1)C.CC(N(C)C)=O.O1CCOCC1>[C:10]([O:14][C:15]([N:17]1[CH2:18][CH:19]2[C:25](=[C:26]([F:27])[C:28](=[O:29])[NH:40][S:37]([C:36]3[C:35]([Cl:41])=[C:34]([Cl:42])[S:33][C:32]=3[Cl:31])(=[O:38])=[O:39])[CH:23]([CH2:22][CH2:21][CH2:20]2)[CH2:24]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

8

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 684431693-(1,1-Dimethylethyl) 9-(carboxyfluoromethylene)-3-azabicyclo[3.3.1]nonane-3-carboxylateHCID 86597098HCID 86597098, compound

Product 1

HCID 68440920HCID 68440920, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolventHCID 31374DimethylacetamideSolvent

Procedure

69 μl of DIEA are added to a solution of 60 mg of 9-(carboxy-fluoro-methylene)-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester, 71 mg of 2,4,5-trichloro-thiophene-3-sulfonyl amide, 233 μl of PPA and 24 mg of DMAP in 2 ml of DMA, and the mixture obtained is stirred at 40° overnight. The mixture obtained is diluted with 10 ml of EtAc/c-HEX, and washed with 1M NaHSO4 solution. The organic layer obtained is dried and solvent is evaporated. The evaporation residue obtained is subjected to chromatography on silica gel and on Sephadex LH20 (MeOH) and relevant fractions obtained from chromatography are subjected to lyophilisation from dioxane. 9-[1-Fluoro-2-oxo-2-(2,4,5-trichloro-thiophene-3-sulfonylamino)-ethylidene]-3-aza-bicyclo[3.3.1]nonane-3-carboxylic acid tert.-butyl ester in the form of a powder is obtained.

Workup

  1. customthe mixture obtained
  2. customThe mixture obtained
  3. additionis diluted with 10 ml of EtAc/c-HEX
  4. washwashed with 1M NaHSO4 solution
  5. customThe organic layer obtained
  6. customis dried
  7. customsolvent is evaporated
  8. customThe evaporation residue obtained

Sources & evidence

ORD record
ord-18b7bf5dd91b40b7bc510b7cfdf6470c
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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