Water → HCID 66817379, compound

HRID 1755018Notes

Reaction equation

HRID 1755018 reaction equation
[CH:1]1([C:7]2[NH:11][C:10](=[O:12])[C:9]3([CH2:17][CH2:16][N:15]([S:18](/[CH:21]=[CH:22]/[C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH2:32][C@H:33]4[CH2:37][O:36]C(C)(C)[O:34]4)[CH:27]=[CH:26]5)(=[O:20])=[O:19])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+].O>C(Cl)Cl.CO>[CH:1]1([C:7]2[NH:11][C:10](=[O:12])[C:9]3([CH2:17][CH2:16][N:15]([S:18](/[CH:21]=[CH:22]/[C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[N:28]([CH2:32][C@H:33]([OH:34])[CH2:37][OH:36])[CH:27]=[CH:26]5)(=[O:19])=[O:20])[CH2:14][CH2:13]3)[N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66818343HCID 66818343, compound

Product 1

HCID 66817379HCID 66817379, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

2-Cyclohexyl-8-{(E)-2-[1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-indol-5-yl]-ethenesulfonyl}-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (41.9 mg, 0.0755 mmol) was dissolved in a methylene chloride-methanol mixed solution (1:1, 1.5 ml). Trifluoroacetic acid (0.35 ml) was added and the mixture was stirred for two days. A saturated aqueous sodium bicarbonate solution and water were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by P-TLC (ethyl acetate-methanol) to give 2-cyclohexyl-8-{(E)-2-[1-((S)-2,3-dihydroxy-propyl)-1H-indol-5-yl]-ethenesulfonyl}-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (33.4 mg, 86%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by P-TLC (ethyl acetate-methanol)

Sources & evidence

ORD record
ord-bddbdf9d2e1e4c6aa7ae4a7a71a074a6
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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