Potassium Carbonate → HCID 57988955, compound

HRID 1689224Notes

Reaction equation

HRID 1689224 reaction equation
[OH:1][C@H:2]([C:38]1[CH:47]=[CH:46][C:45]([OH:48])=[C:44]2[C:39]=1[CH:40]=[CH:41][C:42](=[O:49])[NH:43]2)[CH2:3][N:4]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]2[CH2:37][CH2:36][C:24]3([O:29][CH2:28][CH2:27][N:26](C(=O)C(F)(F)F)[CH2:25]3)[CH2:23][CH2:22]2)[CH:15]=1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(=O)([O-])[O-].[K+].[K+]>CO.O>[O:29]1[C:24]2([CH2:36][CH2:37][N:21]([CH2:20][C:16]3[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=3)[CH2:13][CH2:12][N:4]([CH2:3][C@H:2]([OH:1])[C:38]3[CH:47]=[CH:46][C:45]([OH:48])=[C:44]4[C:39]=3[CH:40]=[CH:41][C:42](=[O:49])[NH:43]4)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:22][CH2:23]2)[CH2:25][NH:26][CH2:27][CH2:28]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57989286HCID 57989286, compound

Product 1

HCID 57988955HCID 57988955, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of (R)-tert-butyl 2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl(3-((4-(2,2,2-trifluoroacetyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethyl)carbamate (example 12, step g) (0.100 g) in methanol (5.0 mL) was treated with a solution of potassium carbonate (0.035 g) in water (5.0 mL) and the resultant mixture stirred at 20° C. for 5 hours. The methanol was evaporated off under a stream of nitrogen and further water (5.0 mL) was added. The solution was acidified by addition of acetic acid and then passed through a 10 g cartridge of C18 silica. The cartridge was washed with water and then flushed with methanol to bring off the product. The solvent was evaporated off under reduced pressure to yield 0.090 g of the acetic acid salt. This solid was dissolved in methanol (2 mL) and passed through 0.700 g of VARIAN Bond Elut NH2 resin and the solvent was evaporated off under reduced pressure to afford the subtitled compound. Yield 0.074 g.

Workup

  1. customThe methanol was evaporated off under a stream of nitrogen and further water (5.0 mL)
  2. additionwas added
  3. additionThe solution was acidified by addition of acetic acid
  4. washThe cartridge was washed with water
  5. customflushed with methanol
  6. customThe solvent was evaporated off under reduced pressure
  7. customto yield 0.090 g of the acetic acid salt
  8. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-8f24c75c1dc84a4ebb69399f9432b8a8
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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