Chloroform → HCID 19802764, compound

HRID 1645959Notes

Reaction equation

[C:1]([NH:9][N:10]=[C:11](OCC)[CH2:12][CH2:13][CH2:14][CH3:15])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][C:21]1[CH:38]=[CH:37][C:24]([O:25][CH:26]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]([O:29][CH3:30])=[O:28])=[C:23]([CH2:39][CH2:40][CH3:41])[CH:22]=1.C(Cl)(Cl)Cl>C(O)C>[CH2:12]([C:11]1[N:19]([CH2:20][C:21]2[CH:38]=[CH:37][C:24]([O:25][CH:26]([C:27]([O:29][CH3:30])=[O:28])[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:23]([CH2:39][CH2:40][CH3:41])[CH:22]=2)[C:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][N:10]=1)[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 43.2 mg (0.175 mmol) of ethyl valerate benzoylhydrazone (from Step K) in 0.2 ml of ethanol was added a solution of 82 mg (0.262 mmol) of methyl 2-(4-aminomethyl-2-propylphenoxy)-2-phenylacetate (from Step J) in 0.2 ml of ethanol. The resulting solution was stirred under N2 at 50° C. for 5.5 hours. After dilution with 0.4 ml of ethanol, the solution was then stirred at 70° C. under a condenser for 13 hours. Next, the solution was co-evaporated with CHCl3. The residue was chromatographed twice in silica gel columns (gradient elution, first with 0.5-3% and then with 0.3-2% MeOH in CHCl2) to give 32 mg (37%) of the title compound as a white glass; homogeneous by TLC in 9:1 CH2Cl2 -MeOH.

Workup

customThe residue was chromatographed twice in silica gel columns (
washgradient elution

Sources & evidence

ORD record: ord-d81119bf06f64e27b0a1c8b1d9db004f
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05177095

Reaction notes

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