Dichloromethane → HCID 11608927, compound

HRID 916363Notes

Reaction equation

HRID 916363 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([NH:13][C@H:14]2[CH2:19][CH2:18][C@H:17](OS(C)(=O)=O)[CH2:16][CH2:15]2)=[CH:5][CH:4]=1)#[N:2].CC(C)([O-])C.[K+].[Cl:31]CCl>CN(C=O)C.C1(C)C=CC=CC=1>[ClH:31].[CH:17]12[N:13]([C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)[CH:14]([CH2:19][CH2:18]1)[CH2:15][CH2:16]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 23665647Potassium tert-butoxide2×HCID 178505323HCID 178505323, compound

Product 1

HCID 11608927HCID 11608927, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21735183Dimethylformamide tolueneSolvent

Procedure

165RL97 (129 mg, 374 μmol) was stirred in DMF/toluene (1:1, 20 mL) at −40° C. and potassium tert-butoxide (42 mg, 374 μmol) was added. The stirring was continued for 30 min before the reaction mixture was brought to rt. After 2 hours, more potassium tert-butoxide (20 mg, 0.18 mol) was added and the reaction was stirred overnight. The mixture was diluted with dichloromethane (50 mL) and washed with water (3×30 mL). The organic layer was dried over sodium sulfate, filtered and evaporated and the residue purified by column chromatography on silica gel using dichloromethane as eluent, yielding the desired compound (67.8 mg, 73%).

Workup

  1. customwas brought to rt
  2. waitAfter 2 hours
  3. washwashed with water (3×30 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f81bab18da4c42e89f58b349b0c833bf
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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