Trifluoroacetic acid → HCID 18727251, compound

HRID 843009Notes

Reaction equation

HRID 843009 reaction equation
[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14][N:13]1[S:25]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]2[C:42]3[C:37](=[C:38]([F:46])[C:39]([F:45])=[C:40]([F:44])[C:41]=3[F:43])[NH:36][CH:35]=2)[CH2:30][CH2:29]1)(=[O:27])=[O:26])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][NH:9][C:10]([C@H:12]1[CH2:17][NH:16][CH2:15][CH2:14][N:13]1[S:25]([N:28]1[CH2:33][CH2:32][CH:31]([C:34]2[C:42]3[C:37](=[C:38]([F:46])[C:39]([F:45])=[C:40]([F:44])[C:41]=3[F:43])[NH:36][CH:35]=2)[CH2:30][CH2:29]1)(=[O:27])=[O:26])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18727258HCID 18727258, compound

Product 1

HCID 18727251HCID 18727251, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyloxy-4-tert-butoxycarbonyl-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide (24.40 g, 36.40 mmol) [prepared as described in Step 4 above] in methylene chloride (90 ml) was added trifluoroacetic acid (60 ml). The reaction mixture was stirred for 2 h, concentrated in vacuo, and partitioned between ethyl acetate (500 ml) and sat. sodium bicarbonate (200 ml). The aqueous layer was washed with ethyl acetate and the combined organic layers were dried over MgSO4 and concentrated in vacuo. The residue was dissolved in ethyl acetate (40 ml) and slowly added to hexane (200 ml) with vigorous stirring. The resulting slurry was filtered to afford 20.65 g of N-benzyloxy-1-[4-(4,5,6,7-tetrafluoroindol-3-yl)piperidine-1-sulfonyl]piperazine-2-(R)-carboxamide as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between ethyl acetate (500 ml) and sat. sodium bicarbonate (200 ml)
  3. washThe aqueous layer was washed with ethyl acetate
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in ethyl acetate (40 ml)
  7. additionslowly added to hexane (200 ml) with vigorous stirring
  8. filtrationThe resulting slurry was filtered

Sources & evidence

ORD record
ord-e86d3175f445475b8f378041f079f892
Source dataset
uspto-grants-2002_04
Patent number
US06376506B1

Reaction notes

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