Methyl 2-(bromomethyl)-6-methylbenzoate → Rac-cis-2-[3-[2-(4-fluorophenyl)oxazol-4-ylmethoxy]cyclohexylmethoxymethyl]-6-methylbenzoic acid

HRID 1168440Notes

Reaction equation

HRID 1168440 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][C@H:5]([OH:9])[CH2:4]1.Br[CH2:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:13]=1[C:14]([O:16]C)=[O:15].[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][CH:32]=[C:33]([CH2:35]I)[N:34]=2)=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[O:31][CH:32]=[C:33]([CH2:35][O:9][C@@H:5]3[CH2:6][CH2:7][CH2:8][C@H:3]([CH2:2][O:1][CH2:11][C:12]4[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:13]=4[C:14]([OH:16])=[O:15])[CH2:4]3)[N:34]=2)=[CH:28][CH:29]=1

Participants

4

Reactant 3

HCID 10263795Methyl 2-(bromomethyl)-6-methylbenzoateHCID 15727328rel-(1R,3S)-3-HydroxycyclohexanemethanolHCID 219802982-(4-Fluorophenyl)-4-(iodomethyl)oxazole

Product 1

HCID 131724079Rac-cis-2-[3-[2-(4-fluorophenyl)oxazol-4-ylmethoxy]cyclohexylmethoxymethyl]-6-methylbenzoic acid

Procedure

Reacting cis-3-hydroxymethylcyclohexanol, bromide 4 and iodide 2 in a reverse order relative to Example XXIV gave the product 41 of molecular weight 453.52 (C26H28FNO5); MS(ESI): 454 (M+H+).

Sources & evidence

ORD record
ord-d25da96f730b4bd2ae4a31651a0f20ab
Source dataset
uspto-grants-2003_09
Patent number
US06624185B2

Reaction notes

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