HCID 59389238, compound → HCID 11175503, compound

HRID 2358304Notes

Reaction equation

HRID 2358304 reaction equation
[NH2:1][CH:2]([CH2:25][O:26][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24]>C1COCC1>[NH2:1][CH:2]([CH2:25][OH:26])[CH2:3][N:4]1[C:13]([C:14]#[N:15])=[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:22][CH3:23])[CH:10]=2)[C:5]1=[O:24]

Participants

3

Reactant 1

HCID 59389238HCID 59389238, compound

Product 1

HCID 11175503HCID 11175503, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 94 (37 mg, 0.063 mmol) in THF at room temperature was added 1M TBAY in THF (1.5 mL). After 2 h, the reaction mixture was partitioned between EtOAc and 1N HCl. The organic phase was washed once with 1N HCl. The combined aqueous phases were basified with NaOH, then extracted with CH2Cl2 (3×). Drying the organic phase (Na2SO4) and concentration gave a residue which was purified by high pressure flash chromatography (0-10% MeOH(NH3)/EtOAc) to give 95.

Workup

  1. customthe reaction mixture was partitioned between EtOAc and 1N HCl
  2. washThe organic phase was washed once with 1N HCl
  3. extractionextracted with CH2Cl2 (3×)
  4. customDrying
  5. concentrationthe organic phase (Na2SO4) and concentration
  6. customgave a residue which
  7. customwas purified by high pressure flash chromatography (0-10% MeOH(NH3)/EtOAc)

Sources & evidence

ORD record
ord-1b35c5c09dff4f539fa2918d16e81b26
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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