Hydrochloric Acid → HCID 67265781, compound

HRID 1685798Notes

Reaction equation

HRID 1685798 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][NH:6][C:7](=[O:31])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:18]=[C:17]([C:19]3[S:20][C:21]([CH2:25][N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])=[C:22]([CH3:24])[CH:23]=3)[O:16][N:15]=2)=[CH:10][CH:9]=1)C.Cl>[Li+].[OH-].CO>[CH2:27]([N:26]([CH2:25][C:21]1[S:20][C:19]([C:17]2[O:16][N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([C:7]([NH:6][CH2:5][C:4]([OH:32])=[O:3])=[O:31])=[CH:9][CH:10]=3)[N:18]=2)=[CH:23][C:22]=1[CH3:24])[CH2:29][CH3:30])[CH3:28]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67265489HCID 67265489, compound

Product 1

HCID 67265781HCID 67265781, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3939Lithium HydroxideSolvent

Procedure

A solution of {4-[5-(5-diethylaminomethyl-4-methyl-thiophen-2-yl)-[1,2,4]oxadiazol-3-yl]-benzoylamino}-acetic acid ethyl ester (105 mg, 230 μmol) in 2 M LiOH in methanol (10 mL) is stirred at rt for 20 h. The mixture is acidified by adding aq. HCl before it is extracted twice with EA. The aq. solution is neutralised by adding sat. aq. NaHCO3 solution and concentrated. The remaining solid is suspended in methanol, filtered and the filtrate is concentrated. The remaining residue is again suspended in a small volume of methanol, filtered and the filtrate is again concentrated. The crude product is purified by CC on silica gel eluting with DCM containing 20% of methanol to give the title compound (30 mg) as a white solid; LC-MS: tR=0.48 min; [M+1]+=429.09; 1H NMR (D6-DMSO): δ1.04 (t, J=7.0 Hz, 6H), 2.23 (s, 3H), 2.58 (q, J=7.3 Hz, 4H), 3.60 (d, J=4.8 Hz, 2H), 3.74 (s, 2H), 7.84 (s, 1H), 8.02-8.07 (m, 2H), 8.10-8.15 (m, 2H), 8.17 (t, J=4.5 Hz, 1H).

Workup

  1. extractionis extracted twice with EA
  2. additionby adding sat. aq. NaHCO3 solution
  3. concentrationconcentrated
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated
  6. filtrationfiltered
  7. concentrationthe filtrate is again concentrated
  8. customThe crude product is purified by CC on silica gel eluting with DCM containing 20% of methanol

Sources & evidence

ORD record
ord-d1a15e72e6d84aa0872e01b495210aff
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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