HCID 131728034, compound → HCID 58922464, compound

HRID 639165Notes

Reaction equation

HRID 639165 reaction equation
C[Si](C)(C)CC[C:5]1([C:36]([O-:38])=[O:37])[CH:10]([CH3:11])[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:8]([NH2:22])=[C:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:6]1[C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1>O1CCCC1>[NH2:22][C:8]1[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:10]([CH3:11])=[C:5]([C:36]([OH:38])=[O:37])[CH:6]([C:28]2[CH:29]=[CH:30][C:31]([C:34]#[N:35])=[CH:32][CH:33]=2)[C:7]=1[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

3

Reactant 1

HCID 131728034HCID 131728034, compound

Product 1

HCID 58922464HCID 58922464, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 410 mg (0.72 mmol) of the compound of Example 58 in 1.4 ml absolute tetrahydrofuran are added 1.43 ml (1.43 mmol) of a 1 M solution of N,N-tributyl-1-butanaminiumfluoride in tetrahydrofuran under argon at 0° C. After 5 minutes at 0° C., the reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue is purified by column chromatography on silica with dichloromethane/methanol 100:1→100:6 mixtures as eluent. The product containing fractions are combined and concentrated in vacuo. The residue is dissolved in 250 ml ethyl acetate and washed three times with 10% citric acid solution and brine. The organic phase is dried with magnesium sulfate and concentrated in vacuo. Trituration of the residue in ethyl acetate affords the title product.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by column chromatography on silica with dichloromethane/methanol 100:1→100:6 mixtures as eluent
  3. additionThe product containing fractions
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue is dissolved in 250 ml ethyl acetate
  6. washwashed three times with 10% citric acid solution and brine
  7. dry with materialThe organic phase is dried with magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f3265e1aed3d4a40b7db0aed833bdc63
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

Loading…