Potassium Carbonate → HCID 69686403, compound

HRID 1018364Notes

Reaction equation

HRID 1018364 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH:7]([O:41]C(=O)C)[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([C:18]2[N:19]=[C:20]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[NH:21][C:22]=2[CH2:23][CH2:24][C:25]23[CH2:34][CH:29]4[CH2:30][CH:31]([CH2:33][CH:27]([CH2:28]4)[CH2:26]2)[CH2:32]3)=[O:17])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[C:1]([O:5][C:6](=[O:45])[CH:7]([OH:41])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]([C:18]2[N:19]=[C:20]([CH:35]3[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]3)[NH:21][C:22]=2[CH2:23][CH2:24][C:25]23[CH2:32][CH:31]4[CH2:33][CH:27]([CH2:28][CH:29]([CH2:30]4)[CH2:34]2)[CH2:26]3)=[O:17])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 70120561HCID 70120561, compound

Product 1

HCID 69686403HCID 69686403, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the product of step c (282 mg, 0.46 mmol) and potassium carbonate (96 mg, 0.70 mmol) in methanol (3 ml) and water (0.3 ml) was stirred at room temperature for 3 h. The reaction was quenched with 10% aqueous citric acid (1 ml), then diluted with ethyl acetate (20 ml). The organic phase was washed with water (20 ml), brine (20 ml), dried (MgSO4) and the solvent was evaporated. The residue was purified by flash chromatography (silica, hexane/ethyl acetate 2:1) to afford colourless foam (167 mg, 63%). 1H NMR (300 MHz, CDCl3) 9.05 (1H, br s), 8.62 (1H, br s), 7.60 (2H, m), 7.25 (1H, m), 6.98 (1H, d), 4.34 (1H, m), 3.13-3.02 (4H, m), 2.93 (1H, m), 2.85 (1H, d), 2.68 (1H, m), 2.05-1.35 (36H, m).

Workup

  1. customThe reaction was quenched with 10% aqueous citric acid (1 ml)
  2. additiondiluted with ethyl acetate (20 ml)
  3. washThe organic phase was washed with water (20 ml), brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated
  6. customThe residue was purified by flash chromatography (silica, hexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-4f03feffd8634372871071951862da85
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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