Ethanol → 7-(4-(6-Tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylic acid

HRID 1626463Notes

Reaction equation

HRID 1626463 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][C:12]([C:14]2[CH:36]=[CH:35][C:17]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]([C:29]([O:31]CC)=[O:30])[CH2:24][CH2:25][O:26]4)=[CH:21][C:20]=3[Cl:34])=[CH:16][CH:15]=2)=[O:13])[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)C>C1COCC1.Cl.C(OCC)(=O)C>[C:1]([C:5]1[N:10]=[C:9]([NH:11][C:12]([C:14]2[CH:36]=[CH:35][C:17]([O:18][C:19]3[CH:28]=[C:27]4[C:22]([CH:23]([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][O:26]4)=[CH:21][C:20]=3[Cl:34])=[CH:16][CH:15]=2)=[O:13])[CH:8]=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67288407Ethyl 7-(4-(6-tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate

Product 1

HCID 672884497-(4-(6-Tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylic acidYield 8.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-(4-(6-tert-butylpyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (10 mg, 0.020 mmol) was diluted with THF (200 μL) followed by the addition of NaOH (98 μL, 0.098 mmol) and ethanol (100 μL). After stirring for 3 hours, the reaction was diluted with 0.5N HCl and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified using a 0.5 mm preparative TLC plate, eluting with 10% methanol/DCM to yield the desired compound (0.8 mg, 0.0017 mmol, 8.5% yield). MS (ESI)=481.2 (M+H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe material was purified
  6. washeluting with 10% methanol/DCM

Sources & evidence

ORD record
ord-3fa933dd096c4903b2f87eab7b51f1a9
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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