Potassium Carbonate → HCID 50943969, compound

HRID 2045801Notes

Reaction equation

HRID 2045801 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1)#[N:2].[OH-].[Na+].C([O-])([O-])=[O:44].[K+].[K+]>C(O)(C)(C)C>[CH3:34][C:26]1[N:25]([CH:20]2[CH2:21][C@H:22]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:6]4[CH:7]=[CH:8][C:3]([C:1]([NH2:2])=[O:44])=[CH:4][CH:5]=4)(=[O:10])=[O:11])[C@H:18]([CH2:24][CH2:23]3)[CH2:19]2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 50943880HCID 50943880, compound

Product 1

HCID 50943969HCID 50943969, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a suspension of the title compound from example 4 (63 mg, 0.11 mmol) in t-butanol (1 mL) was added 1M NaOH (0.28 mL) and the reaction stirred at room temperature for 2 h, followed by heating to 80° C. for 2 h. The reaction was cooled to room temperature and partitioned between ethyl acetate and pH 8 buffer solution. 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 (40 mg, 63% yield) was obtained as a white solid (free-based with K2CO3).

Workup

  1. temperatureby heating to 80° C. for 2 h
  2. temperatureThe reaction was cooled to room temperature
  3. custompartitioned between ethyl acetate and pH 8 buffer solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse-phase HPLC
  7. washeluting with 10-90% water/acetonitrile/0.1% TFA

Sources & evidence

ORD record
ord-37562c80372542f295948a9012a0f537
Source dataset
uspto-grants-2013_11
Patent number
US08592395B2

Reaction notes

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