Methyl (2S)-methoxy(phenyl)ethanoate → 2-(Methoxy-phenyl-methyl)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Trifluoroacetate

HRID 2053632Notes

Reaction equation

C[Al](C)C.COC(=O)[C@@H](OC)C1C=CC=CC=1.[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21].[CH3:25][O:26][CH:27]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:28]1[NH:29][CH:30]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:32]=1>>[F:18][C:19]([F:24])([F:23])[C:20]([OH:22])=[O:21].[CH3:25][O:26][CH:27]([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:28]1[NH:32][C@H:31]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C@H:30]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[N:29]=1

Participants

Reactant 3

HCID 11446684Methyl (2S)-methoxy(phenyl)ethanoate

HCID 16682925Trimethylaluminum

HCID 68567187HCID 68567187, compound

Product 1

HCID 685698772-(Methoxy-phenyl-methyl)-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Trifluoroacetate

Procedure

Employing the general trimethylaluminum coupling procedure and using methoxy-(S)-phenyl-acetic acid methyl ester prepared in accordance with Step 1 as described above and meso-1,2-diphenylethylene-diamine there was made, 2-(Methoxy-phenyl-methyl)-4,5-diphenyl-4,5-dihydro-1H-imidazole trifluoroacetate. 1H NMR (DMSO) δ 11.11 (bs, 1H), 7.7-7.5 (m, 5H), 7.1-7.0 (m, 6H), 6.90-6.85 (m, 2H), 6.8-6.7 (m, 2H), 5.81 (s, 2H), 5.65 (s, 1H), 3.49 (s, 3H); LC/MS: 3.69 min/m/z 343 (M++1)

Workup

customprepared in accordance with Step 1

Sources & evidence

ORD record: ord-76cce54c08f94075ac75927bff57c3b4
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326792B2

Reaction notes

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