Trifluoroacetic acid → HCID 24899028, compound

HRID 555365Notes

Reaction equation

HRID 555365 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][CH2:10]/[C:11](/[CH2:27][O:28][C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:32]=[CH:31][CH:30]=2)=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([NH:19][O:20]C2CCCCO2)=[O:18])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>CO>[OH:20][NH:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13]/[CH:12]=[C:11](\[CH2:27][O:28][C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)/[CH2:10][NH:9][CH2:8][CH2:7][N:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86640101HCID 86640101, compound

Product 1

HCID 24899028HCID 24899028, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-8-(2-morpholinoethylamino)-7-((naphthalen-1-yloxy)methyl)-N-(tetrahydro-2H-furan-2-yloxy)oct-6-enamide (63 mg, 0.09 mmol) obtained in Example (3-1-3) was dissolved in methanol (1.5 ml), and trifluoroacetic acid (0.04 ml, 0.45 mmol) was slowly added thereto at room temperature. The resulting mixture was reacted for 8 hours to conduct a deprotection reaction of THP. After the completion of reaction, the reaction solution was concentrated under reduced pressure. The residue thus obtained was purified by a preparative HPLC to obtain 21 mg of the title compound as pale orange oil (yield 53%), which was used in the subsequent analysis.

Workup

  1. customat room temperature
  2. customThe resulting mixture was reacted for 8 hours
  3. customa deprotection reaction of THP
  4. customAfter the completion of reaction
  5. concentrationthe reaction solution was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by a preparative HPLC

Sources & evidence

ORD record
ord-eb9250d565154f3589d1554cbc0260f1
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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