Potassium Carbonate → HCID 68677180, compound

HRID 1158512Notes

Reaction equation

HRID 1158512 reaction equation
[CH3:1][O:2][C:3](=[O:41])[NH:4][C@H:5]([C:10]([NH:12][NH:13][CH2:14][CH2:15][C@:16]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([OH:33])[C:17]([N:19]1[C@H:23]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=3[CH2:30][C@H:22]2[O:21]C1(C)C)=[O:18])=[O:11])[C:6]([CH3:9])([CH3:8])[CH3:7].C([O-])([O-])=O.[K+].[K+].[Br:48][C:49]1[CH:56]=[CH:55][C:52]([CH2:53]Br)=[CH:51][CH:50]=1>CC(=O)CC>[CH3:1][O:2][C:3](=[O:41])[NH:4][C@@H:5]([C:10]([NH:12][N:13]([CH2:53][C:52]1[CH:55]=[CH:56][C:49]([Br:48])=[CH:50][CH:51]=1)[CH2:14][CH2:15][C@@:16]([OH:33])([C:17](=[O:18])[NH:19][C@H:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30][C@H:22]1[OH:21])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:11])[C:6]([CH3:7])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 68676597HCID 68676597, compound

Product 1

HCID 68677180HCID 68677180, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

Compound 21i (0.105 g) was dissolved in 2-butanone (10 mL) and added K2CO3 (0.045 g, 0.32 mmol), and 4-bromobenzyl bromide (0.054 g, 0.21 mmol) and stirred at 80° C. for 3 h. Solvent was evaporated and the residue was dissolved in dichloromethane (15 mL), washed with water, brine and cooled to 0° C. TFA (1.0 mL) was added slowly and stirred for 30 min then evaporated. Residue dissolved in dichloromethane (10 mL) and washed with NaHCO3 solution, water, brine and dried. Residue was purified by analytical preparative LCMS to yield 0.023 g (15% overall yield) of the title compound.

Workup

  1. customSolvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane (15 mL)
  3. washwashed with water, brine
  4. temperaturecooled to 0° C
  5. additionTFA (1.0 mL) was added slowly
  6. stirringstirred for 30 min
  7. customthen evaporated
  8. dissolutionResidue dissolved in dichloromethane (10 mL)
  9. washwashed with NaHCO3 solution, water, brine
  10. customdried
  11. customResidue was purified by analytical preparative LCMS
  12. customto yield

Sources & evidence

ORD record
ord-a0e74bf6989d48b1af6572493d9a6286
Source dataset
uspto-grants-2010_10
Patent number
US07807677B2

Reaction notes

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