Potassium Hydroxide → HCID 58930469, compound

HRID 416297Notes

Reaction equation

HRID 416297 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C@H:11]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22](=[O:31])[NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[NH2:30])=[CH:18][CH:17]=3)[CH2:12]2)=[CH:6][CH:5]=1.[OH-].[K+]>C1COCC1.O.CO>[NH2:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][C:22]([C:19]1[CH:18]=[CH:17][C:16]([N:13]2[CH2:14][CH2:15][C@H:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=3)[CH2:12]2)=[CH:21][CH:20]=1)=[O:31]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 58930630HCID 58930630, compound

Product 1

HCID 58930469HCID 58930469, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 372 (100 mg, 0.23 mmol) and KOH (100 mg, 1.78 mmol) in 1:1:1 mixture of THF/water/MeOH (6 mL) was stirred at room temperature for 5 days. The reaction mixture was concentrated and partitioned between water (5 mL) and ether (5 mL). Organic phase was discarded and the aqueous phase was acidified to pH=6 using 1M HCl solution and extracted with EtOAc. The extract was dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography, eluent MeOH-DCM (gradient of MeOH from 5 till 20% MeOH) to afford the title compound (20 mg, 21% yield). 1H NMR (DMSO) δ 9.34 (σ, 1H), 7.85 (m, 4H), 7.11 (d, 1H, J=7.8 Hz), 7.00 (d, J=8.4 Hz, 2H), 6.92 (d, 2H, J=7.7 Hz), 6.75 (d, J=8.0 Hz, 2H), 6.6 (m, 3H), 5.26 (br.s., 1H), 3.75 (m, 1H), [3.34 DMSO, 4H], 2.44 (m, 1H), 2.31 (m, 1H) m/z: 418.4 (MH+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between water (5 mL) and ether (5 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe extract was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography, eluent MeOH-DCM (gradient of MeOH from 5 till 20% MeOH)

Sources & evidence

ORD record
ord-0535665f071d48ea947eb94c2a758f5a
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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