Potassium Carbonate → HCID 50943967, compound

HRID 2045800Notes

Reaction equation

HRID 2045800 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:9]([NH:12][CH2:13][CH:14]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:15][CH2:16][N:17]2[C@H:22]3[CH2:23][CH2:24][C@@H:18]2[CH2:19][CH:20]([N:25]2[C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=4[N:27]=[C:26]2[CH3:34])[CH2:21]3)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1)#[N:2].OO.NC(N)=[O:45].C([O-])([O-])=O.[K+].[K+]>CC(C)=O.O>[CH3:34][C:26]1[N:25]([CH:20]2[CH2:19][C@H:18]3[N:17]([CH2:16][CH2:15][CH:14]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:13][NH:12][S:9]([C:5]4[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=4)[C:1]([NH2:2])=[O:45])(=[O:10])=[O:11])[C@H:22]([CH2:23][CH2:24]3)[CH2:21]2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 31294Carbamide PeroxideHCID 50943879HCID 50943879, compound

Product 1

HCID 50943967HCID 50943967, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

The title compound from example 3 (65 mg, 0.12 mmol) was dissolved in acetone (1 mL) and water (0.5 mL). To the solution was added urea hydrogen peroxide (110 mg, 1.2 mmol) followed by K2CO3 (5 mg, 0.036 mmol) and the reaction stirred at room temperature for 2 h, whereupon the reaction was found to be mostly complete by LC-MS. The reaction was poured into water and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse-phase HPLC eluting with 10-90% water/acetonitrile/0.1% TFA. The title compound (37 mg, 54% yield) was obtained as a white solid (free-based with K2CO3).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by reverse-phase
  5. washHPLC eluting with 10-90% water/acetonitrile/0.1% TFA

Sources & evidence

ORD record
ord-a1ac96cc146a44fc928b20e4a776b3b8
Source dataset
uspto-grants-2013_11
Patent number
US08592395B2

Reaction notes

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