Sodium Hydroxide → HCID 66817821, compound

HRID 1755120Notes

Reaction equation

HRID 1755120 reaction equation
[C:1]([O:5][C:6](=[O:49])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:23][CH2:22][C:21]([NH:27][C:28](=O)[C:29]3[CH:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:32]=[C:31]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[CH:30]=3)([C:24](=[O:26])[NH2:25])[CH2:20][CH2:19]2)(=[O:17])=[O:16])=[C:9]([CH3:48])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[Cl-].[NH4+]>CO>[C:1]([O:5][C:6](=[O:49])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][S:15]([N:18]2[CH2:23][CH2:22][C:21]3([N:27]=[C:28]([C:29]4[CH:34]=[C:33]([C:35]([F:37])([F:36])[F:38])[CH:32]=[C:31]([O:39][CH2:40][C:41]5[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=5)[CH:30]=4)[NH:25][C:24]3=[O:26])[CH2:20][CH2:19]2)(=[O:16])=[O:17])=[C:9]([CH3:48])[CH:8]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66816874HCID 66816874, compound

Product 1

HCID 66817821HCID 66817821, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4-{2-[4-(3-Benzyloxy-5-trifluoromethyl-benzoylamino)-4-carbamoyl-piperidine-1-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester (1.23 g, 1.75 mmol) was dissolved in methanol (17.5 ml). A 1 M aqueous sodium hydroxide solution (1.75 ml, 1.75 mmol) was added and the mixture was stirred at 60° C. for six hours. After completion of the reaction, the reaction solution was left to cool and an aqueous ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saline, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue obtained by concentration was purified by column chromatography (hexane:ethyl acetate) to give 4-{2-[2-(3-benzyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid tert-butyl ester as a pale yellow amorphous (952.1 mg, yield in two steps: 79.3%).

Workup

  1. customAfter completion of the reaction
  2. waitthe reaction solution was left
  3. temperatureto cool
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained by concentration
  9. customwas purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-bc783dabe2ee4b83ab5e1e0f717d9bc1
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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