HCID 86628454, compound → HCID 25164758, compound

HRID 1943351Notes

Reaction equation

HRID 1943351 reaction equation
FC(F)(F)C([NH:5][CH2:6][CH2:7][CH:8]([OH:24])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]#[C:16][C:17]2([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:10]=1)=O>CO.O>[NH2:5][CH2:6][CH2:7][CH:8]([C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]2([OH:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH:12]=[CH:13][CH:14]=1)[OH:24]

Participants

3

Reactant 1

HCID 86628454HCID 86628454, compound

Product 1

HCID 25164758HCID 25164758, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Deprotection of 2,2,2-trifluoro-N-(3-hydroxy-3-(3-((1-hydroxycyclohexyl)ethynyl)phenyl)propyl)acetamide was conducted following the method used in Example 18, except that the solvent was 90% MeOH-water and the reaction was stirred overnight. The reaction mixture was concentrated under reduced pressure and partitioned into EtOAc and water. The combined organics were dried over Na2SO4 and concentrated under reduced pressure. The crude material was crystallized from hot EtOAc. After cooling, the product was collected by filtration, washed with EtOAc and hexanes, and dried. Example 99 was isolated as a white solid. Yield (0.210 g, 47%): 1H NMR (400 MHz, DMSO-d6) δ 7.23-7.26 (m, 4H), 5.45 (br s, 1H), 4.68 (t, J=8.4 Hz, 1H), 2.62 (br s, 2H), 1.83-1.88 (m, 2H), 1.48-1.67 (m, 9H), 1.15-1.34 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompartitioned into EtOAc and water
  3. dry with materialThe combined organics were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was crystallized from hot EtOAc
  6. temperatureAfter cooling
  7. filtrationthe product was collected by filtration
  8. washwashed with EtOAc and hexanes
  9. customdried
  10. customExample 99 was isolated as a white solid
  11. customYield (0.210 g, 47%)

Sources & evidence

ORD record
ord-90d0ffa6f4cf4027be179a87f36c77f8
Source dataset
uspto-grants-2013_03
Patent number
US08389771B2

Reaction notes

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