Acetic Acid → Ethyl pentanimidate hydrochloride

HRID 36177Notes

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[N:36]([C:37]([C:50]4[CH:55]=[CH:54][CH:53]=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:35]=[N:34][N:33]=3)=[CH:22][CH:21]=2)[C:7](=[O:18])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:16][OH:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:56](O)(=[O:58])[CH3:57].O.C(Cl)[Cl:62]>CO>[C:56]([O:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:8]1[C:7](=[O:18])[N:6]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[NH:33][N:34]=[N:35][N:36]=3)=[CH:24][CH:25]=2)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9]1)(=[O:58])[CH3:57].[ClH:62].[C:37](=[NH:36])([O:58][CH2:56][CH3:57])[CH2:50][CH2:55][CH2:54][CH3:53]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 35 mg (0.0484 mmole) of 5-n-butyl-2,4-dihydro-2-[2-(hydroxymethyl)phenyl]-4-[[2'-(N-trityltetrazol-5-yl)biphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one, 0.5 mL of glacial acetic acid, and 0.25 mL of H2O was stirred at 60° C. overnight, TLC in 90:10 CH2Cl2 --MeOH showed two products at Rf <0.25. After cooling to room temperature, solvents were evaporated and the residue flash chromatographed over silica gel (gradient elution with 4-10% methanol in CH2Cl2) to give 7 mg of product B (the acetate) as an oil and 12 mg of product A (the hydroxy compound) as a clear oil. Each compound was homogeneous by TLC in 90:10 CH2Cl2 --MeOH, mass spectrum (FAB) for A m/e 482 (M+1)+ and for B m/e 524(M+1)+.

Workup

temperatureAfter cooling to room temperature
customsolvents were evaporated
customthe residue flash chromatographed over silica gel (gradient elution with 4-10% methanol in CH2Cl2)

Sources & evidence

ORD record: ord-02cc1f0f0f154c30b7725dd17b48732f
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05411980

Reaction notes

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