Trifluoroacetic acid → HCID 49847657, compound

HRID 1845956Notes

Reaction equation

HRID 1845956 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[N:23][CH:22]=[CH:21]3)(=[O:17])=[O:16])[C@@H:10]([CH3:28])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:28][C@H:10]1[CH2:9][NH:8][CH2:14][CH2:13][CH2:12][N:11]1[S:15]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[N:23][CH:22]=[CH:21]2)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66727237HCID 66727237, compound

Product 1

HCID 49847657HCID 49847657, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.1 g of (S)-6-(4-tert-butoxycarbonyl-2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline was dissolved in 50 mL of dichloromethane, and 1.8 mL of trifluoroacetic acid was added dropwise thereto at room temperature and then reacted for 6 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane (50 mL×2). The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=10:1:0.05) to obtain 0.4 g of the compound of interest as a white crystal (48%).

Workup

  1. customat room temperature and then reacted for 6 hours
  2. extractionfollowed by extraction with dichloromethane (50 mL×2)
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=10:1:0.05)

Sources & evidence

ORD record
ord-1d82b05492e749faac7b7e0d9e7a2cd6
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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