Ethanol → HCID 44600230, compound

HRID 1021454Notes

Reaction equation

HRID 1021454 reaction equation
[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:34]=[CH:33][C:15]([O:16][C:17]2[CH:26]=[C:25]3[C:20]([CH:21]([C:27]([O:29]CC)=[O:28])[CH2:22][CH2:23][O:24]3)=[CH:19][C:18]=2[Cl:32])=[CH:14][CH:13]=1)=[O:11].[OH-].[Na+].C(O)C>C1COCC1.C(OCC)(=O)C.Cl>[C:1]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[CH:26]=[C:25]3[C:20]([CH:21]([C:27]([OH:29])=[O:28])[CH2:22][CH2:23][O:24]3)=[CH:19][C:18]=2[Cl:32])=[CH:33][CH:34]=1)=[O:11]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67080523HCID 67080523, compound

Product 1

HCID 44600230HCID 44600230, compoundYield 94.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 7-(4-(2-(biphenyl-2-yl)ethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (29 mg, 0.052 mmol) was diluted with THF (1 mL) followed by the addition of NaOH (261 μl, 0.26 mmol) and ethanol (500 μL). After stirring for 2 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 to yield 7-(4-(2-(biphenyl-2-yl)ethylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylic acid (26 mg, 0.049 mmol, 94% yield).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b91a6ec3c813455ca959e1524538d859
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

Loading…