Ethanol → HCID 67288335, compound

HRID 1626489Notes

Reaction equation

HRID 1626489 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:32])[NH:20][C:21]3[S:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:24][N:25]=3)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([O:35]CC)=[O:34].[OH-].[Na+].C(O)C>C1COCC1.C(OCC)(=O)C.Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:19](=[O:32])[NH:20][C:21]3[S:22][C:23]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:24][N:25]=3)=[CH:17][CH:18]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:33]([OH:35])=[O:34]

Participants

7

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 67287467HCID 67287467, compound

Product 1

HCID 67288335HCID 67288335, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 6-chloro-7-(4-(5-phenyl-1,3,4-thiadiazol-2-ylcarbamoyl)phenoxy)chroman-4-carboxylate (17 mg, 0.032 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (159 μL, 0.16 mmol) and ethanol (200 μL). After stirring for 4 hours, the reaction was diluted with ethyl acetate and 1N 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 10% methanol/DCM to yield the desired compound (5 mg, 0.0098 mmol, 31% yield). MS (ESI)=508.1 (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 10% methanol/DCM

Sources & evidence

ORD record
ord-361e3b057e0948648152483059f28d6b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

Loading…