Methanol → HCID 86742612, compound

HRID 414240Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][C:11]([C:25]2[O:26][C:27]([CH2:30][CH3:31])=[N:28][N:29]=2)([N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15](=[O:18])[CH2:16][CH3:17])[CH2:10][CH2:9]1.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].CO>C(OCC)(=O)C>[C:32]([O-:37])(=[O:36])[C:33]([O-:35])=[O:34].[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH+:8]1[CH2:13][CH2:12][C:11]([C:25]2[O:26][C:27]([CH2:30][CH3:31])=[N:28][N:29]=2)([N:14]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15](=[O:18])[CH2:16][CH3:17])[CH2:10][CH2:9]1.[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][NH+:8]1[CH2:9][CH2:10][C:11]([N:14]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:15](=[O:18])[CH2:16][CH3:17])([C:25]2[O:26][C:27]([CH2:30][CH3:31])=[N:28][N:29]=2)[CH2:12][CH2:13]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1-[2-(2-thienyl)ethyl]-4-(ethyl-1,3,4-oxadiazolyl)-4-(N-phenylpropionamido)piperidine (660 mg, 1.50 mmol) in ethyl acetate (20 ml), oxalic acid (136 mg, 1.51 mmol, in 3 ml EtoAc) was added dropwise. The resulting mixture was heated to 70° C. and methanol added dropwise until it became a clear solution. The solution was cooled to room temperature on standing for 2 hours. The precipitate was filtered to afford the product (630 mg, 1.19 mmol) as a white crystalline compound, mp 160°-162° C. Anal. Calcd. for C24H30N4O2S.C2H2O4 : C, 59.07; H, 6.10; H, 10.60 Found: C, 59.08; H, 6.26; N, 10.45. ##STR36##

Workup

temperatureThe solution was cooled to room temperature
filtrationThe precipitate was filtered

Sources & evidence

ORD record: ord-94590e813a9d4b7a90bf17222c4da1dd
Source dataset: uspto-grants-1988_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04791120

Reaction notes

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