Hydrochloric Acid → HCID 86664396, compound

HRID 1626491Notes

Reaction equation

HRID 1626491 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]2[CH:35]=[CH:34][C:16]([O:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]([C:28]([O:30]CC)=[O:29])[CH2:23][CH2:24][O:25]4)=[CH:20][C:19]=3[Cl:33])=[CH:15][CH:14]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.C(O)C.[OH-].[Na+].Cl>C(OCC)(=O)C>[C:1]([C:5]1[N:6]=[C:7]([NH:10][C:11]([C:13]2[CH:14]=[CH:15][C:16]([O:17][C:18]3[CH:27]=[C:26]4[C:21]([CH:22]([C:28]([OH:30])=[O:29])[CH2:23][CH2:24][O:25]4)=[CH:20][C:19]=3[Cl:33])=[CH:34][CH:35]=2)=[O:12])[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21873804Tetrahydrofuran ethanolHCID 86664395HCID 86664395, compound

Product 1

HCID 86664396HCID 86664396, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-(4-(4-tert-butylthiazol-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (408 μl, 0.0408 mmol) in 2:1 THF-Ethanol was treated with 1N sodium hydroxide (0.061 ml, 0.061 mmol) at ambient temperature. After 18 hours, the reaction was diluted with ethyl acetate and acidified with hydrogen chloride (81.6 μl, 0.0816 mmol). The reaction was washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to give the desired product (0.015 g, 76%) as a white solid. MS (APCI)=487.1 (M+1).

Workup

  1. washThe reaction was washed with brine
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf2d2601b6de439b8ae07c1aeb319bf4
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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