Potassium Hydroxide → HCID 58930469, compound

HRID 852968Notes

Reaction equation

HRID 852968 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-8621c726f2d847dcbda150d3b9dc1af2
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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