Cesium carbonate → HCID 71008442, compound

HRID 1845968Notes

Reaction equation

HRID 1845968 reaction equation
BrC1C=CC(S(O[C@H:12]2[CH2:45][N:15]3[C:16](=[O:44])[C@@H:17]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[CH:24][C@@H:25]4[CH2:30][C@@:26]4([C:31]([O:33][CH2:34][CH3:35])=[O:32])[NH:27][C:28](=[O:29])[C@@H:14]3[CH2:13]2)(=O)=O)=CC=1.[F:46][C:47]1[CH:48]=[CH:49][C:50]2[C:59]([CH:60]=1)=[N:58][C:57]([OH:61])=[C:56]1[C:51]=2[CH:52]=[CH:53][CH:54]=[CH:55]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:40]([O:39][C:37]([NH:36][C@@H:17]1[C:16](=[O:44])[N:15]2[CH2:45][C@H:12]([O:61][C:57]3[N:58]=[C:59]4[C:50](=[C:51]5[C:56]=3[CH:55]=[CH:54][CH:53]=[CH:52]5)[CH:49]=[CH:48][C:47]([F:46])=[CH:60]4)[CH2:13][C@H:14]2[C:28](=[O:29])[NH:27][C@:26]2([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:30][C@H:25]2[CH:24]=[CH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86673688HCID 86673688, compoundHCID 178517313HCID 178517313, compound

Product 1

HCID 71008442HCID 71008442, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (2R,6S,13aS,14aR,16aS,Z)-ethyl 2-(4-bromophenylsulfonyloxy)-6-(tert-butoxycarbonylamino)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (1b, 2.3 g, 3.2 mmol), 3-fluorophenanthridin-6-ol (Example 1a, 0.688 g, 3.23 mmol) and cesium carbonate (1.2 g, 3.6 mmol) in dimethylformamide (32 ml) was heated @80° C. for 5 h. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 2 N HCl. The organic phase was washed with water and then saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and evaporated. The resulting solid was purified by flash chromatography on silica gel, eluting with acetone/hexane, to provide the title compound (1.3 g, 60% yield).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between ethyl acetate and 2 N HCl
  3. washThe organic phase was washed with water
  4. dry with materialsaturated aqueous sodium chloride, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting solid was purified by flash chromatography on silica gel
  8. washeluting with acetone/hexane

Sources & evidence

ORD record
ord-41b4737582cc46b4910716656cd12e06
Source dataset
uspto-grants-2015_02
Patent number
US08951964B2

Reaction notes

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