Acetic Acid → HCID 18947607, compound

HRID 1769382Notes

Reaction equation

[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:26]=[CH:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[N:18]=3)=[CH:11][CH:10]=2)N)=[CH:4][CH:3]=1.CC([O-])=O.[Na+].CC(O)=O.[C:38]([S:42][CH2:43][C:44](=O)[CH2:45][C:46]([CH2:53][CH3:54])([CH2:51][CH3:52])[C:47]([O:49][CH3:50])=[O:48])([CH3:41])([CH3:40])[CH3:39]>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:9]3[C:14](=[CH:13][C:12]([O:15][CH2:16][C:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:18]=4)=[CH:11][CH:10]=3)[C:43]([S:42][C:38]([CH3:41])([CH3:40])[CH3:39])=[C:44]2[CH2:45][C:46]([CH2:53][CH3:54])([CH2:51][CH3:52])[C:47]([O:49][CH3:50])=[O:48])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a mixture of 1-(4-chlorobenzyl)-1-[4-(quinolin-2-ylmethoxy)phenyl]hydrazine from Example 1A, Step D, (660 mg, 1.7 mmol) and anhydrous NaOAc (160 mg, 1.95 mmol) in toluene (3 mL) was added glacial HOAc (1.5 mL) . After 30 minutes, a solution containing methyl 5-(t-butylthio)-2,2-diethyl-4-oxopentanoate from Step B (402 mg, 1.47 mmol) in toluene (1 mL) was added and the reaction mixture stirred for 24 hours at room temperature and for 48 hours at 65° C. The reaction was then diluted with EtOAc, washed with NH4OAc buffer (25% w/v) and dried over MgSO4. Filtration and concentration gave a viscous oil which was purifed by flash chromatography on silica gel (eluant:EtOAc-hexane 15:85) to give the title compound.

Workup

additionwas added
washwashed with NH4OAc buffer (25% w/v)
dry with materialdried over MgSO4
filtrationFiltration and concentration
customgave a viscous oil which

Sources & evidence

ORD record: ord-b6432adbf29a4cb383835079e97b95e5
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05380850

Reaction notes

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