HCID 68288804, compound → HCID 66546509, compound

HRID 1853098Notes

Reaction equation

HRID 1853098 reaction equation
[NH2:1][C:2]1[C:3]([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]3[C:37](=[O:49])[N:38]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[N:39]([CH3:42])[C:40]=3[CH3:41])=[O:35])=[CH:29][CH:28]=2)=[N:4][C:5]([CH:8]2[CH2:13][CH2:12][CH2:11][N:10]([C:14](=[O:26])[CH2:15][CH2:16]S(C3C=CC=CC=3)(=O)=O)[CH2:9]2)=[CH:6][N:7]=1.C(O[K])(C)(C)C>C1COCC1>[C:14]([N:10]1[CH2:11][CH2:12][CH2:13][CH:8]([C:5]2[N:4]=[C:3]([C:27]3[CH:28]=[CH:29][C:30]([NH:33][C:34]([C:36]4[C:37](=[O:49])[N:38]([C:43]5[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=5)[N:39]([CH3:42])[C:40]=4[CH3:41])=[O:35])=[CH:31][CH:32]=3)[C:2]([NH2:1])=[N:7][CH:6]=2)[CH2:9]1)(=[O:26])[CH:15]=[CH2:16]

Participants

4

Reactant 2

HCID 68288804HCID 68288804, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 66546509HCID 66546509, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Example 33 (0.0121 g) in anhydrous THF (1.0 mL) at room temperature under N2 was added tBuOK (0.0030 g). The reaction immediately turned yellow, then a darker brown. After 2 hours, the reaction was partitioned between DCM and saturated NaHCO3 solution and separated. The aqueous layer was reextracted with DCM. The organic layers were combined and washed with water, and brine, then dried with Na2SO4 and concentrated. Purification by preparative TLC yielded the title compound (0.0074 g) having the following physical data.

Workup

  1. customThe reaction immediately turned yellow
  2. customthe reaction was partitioned between DCM and saturated NaHCO3 solution
  3. customseparated
  4. washwashed with water, and brine
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customPurification by preparative TLC

Sources & evidence

ORD record
ord-0c99322f0e8947e6b0be10bc09f31ab8
Source dataset
uspto-grants-2015_02
Patent number
US08962623B2

Reaction notes

Loading…