Methanol → 7-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylic acid

HRID 1021370Notes

Reaction equation

HRID 1021370 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:35]=[CH:34][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:28]([O:30]C)=[O:29])[CH2:21][C:22]([CH3:27])([CH3:26])[O:23]4)=[CH:18][C:17]=3[C:32]#[N:33])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.[OH-].[Na+].O.CO>C1COCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([CH:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]([CH3:26])([CH3:27])[O:23]4)=[CH:18][C:17]=3[C:32]#[N:33])=[CH:34][CH:35]=2)=[O:10])=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080218Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylate

Product 1

HCID 670804237-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylic acidYield 30.9%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-2,2-dimethylchroman-4-carboxylate (2.0 mg, 0.00385 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (0.00771 mL, 0.0385 mmol) and 200 μL of water and methanol. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl. 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 5% methanol/0.5% acetic acid/CH2Cl2 to yield the title compound (0.6 mg, 30.8% yield) as a white solid. MS (ESI)=504.9 (M+1).

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 5% methanol/0.5% acetic acid/CH2Cl2

Sources & evidence

ORD record
ord-3598b875ce0940c584a5e054f5e89b78
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

Loading…