Methanol → 7-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyano-4-methylchroman-4-carboxylic acid

HRID 1047991Notes

Reaction equation

HRID 1047991 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH2:7][NH:8][C:9]([C:11]2[CH:34]=[CH:33][C:14]([O:15][C:16]3[CH:25]=[C:24]4[C:19]([C:20]([CH3:30])([C:26]([O:28]C)=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:31]#[N:32])=[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]([C:20]([CH3:30])([C:26]([OH:28])=[O:27])[CH2:21][CH2:22][O:23]4)=[CH:18][C:17]=3[C:31]#[N:32])=[CH:33][CH:34]=2)=[O:10])=[CH:35][CH:36]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080322Methyl 7-(4-((4-chlorophenethyl)carbamoyl) phenoxy)-6-cyano-4-methylchroman-4-carboxylate

Product 1

HCID 670804267-(4-((4-Chlorophenethyl)carbamoyl)phenoxy)-6-cyano-4-methylchroman-4-carboxylic acidYield 34.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 7-(4-((4-chlorophenethyl)carbamoyl)phenoxy)-6-cyano-4-methylchroman-4-carboxylate (12 mg, 0.0238 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (0.0475 mL, 0.238 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 the Horizon with a 25 cartridge and running a gradient 0.5% methanol/0.5% acetic acid/CH2Cl2 to 10% methanol/0.5% acetic acid/CH2Cl2 to yield the title compound (4.0 mg, 34.3% yield) as a white solid. MS (ESI)=490.9 (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

Sources & evidence

ORD record
ord-e9ef8a6dab514d68ac55102a35e4c88b
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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