Potassium Carbonate → HCID 58392822, compound

HRID 446839Notes

Reaction equation

HRID 446839 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][N:6]1[CH2:30][C@:29]2([C:31](=[O:37])[CH2:32][O:33]C(=O)C)[C@@H:8]([CH2:9][C@H:10]3[C@H:23]4[C@@:14]([F:27])([C@:15]5([CH3:26])[C:20]([C@@H:21]([F:24])[CH2:22]4)=[CH:19][C:18](=[O:25])[CH:17]=[CH:16]5)[C@@H:13]([OH:28])[CH2:12][C@@:11]32[CH3:38])[CH2:7]1)[CH3:2].C([O-])([O-])=O.[K+].[K+]>C(O)C>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][N:6]1[CH2:30][C@:29]2([C:31](=[O:37])[CH2:32][OH:33])[C@@H:8]([CH2:9][C@H:10]3[C@H:23]4[C@@:14]([F:27])([C@:15]5([CH3:26])[C:20]([C@@H:21]([F:24])[CH2:22]4)=[CH:19][C:18](=[O:25])[CH:17]=[CH:16]5)[C@@H:13]([OH:28])[CH2:12][C@@:11]32[CH3:38])[CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58392724HCID 58392724, compound

Product 1

HCID 58392822HCID 58392822, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 158 (75 mg, 0.136 mmol) in ethanol (5 ml) is degassed with nitrogen for 15 minutes and cooled to 0° C. Then K2CO3 (9.43 mg, 0.068 mmol) is added and the mixture is stirred at 0° C. with continuous degassing for 1 hour. The reaction mixture is partitioned between water and AcOEt. The combined organic phases are concentrated and crude is purified by silica gel flash chromatography (eluent DCM/EtOH=99/1 to 95/5) to yield the title compound (31 mg, 0.061 mmol, 45% yield).

Workup

  1. customwith continuous degassing for 1 hour
  2. customThe reaction mixture is partitioned between water and AcOEt
  3. concentrationThe combined organic phases are concentrated
  4. customcrude is purified by silica gel flash chromatography (eluent DCM/EtOH=99/1 to 95/5)

Sources & evidence

ORD record
ord-83f26b411ec84a42b4ce0b65cb4c71b4
Source dataset
uspto-grants-2013_07
Patent number
US08481517B2

Reaction notes

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