Triethylamine → (2-Methylbenzenesulfonyl)-carbamic Acid 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyl Ester

HRID 11646Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([CH2:28][OH:29])[CH:3]=1.C(N(CC)CC)C.[C:37]1([CH3:49])[C:38]([S:43]([N:46]=[C:47]=[O:48])(=[O:45])=[O:44])=[CH:39][CH:40]=[CH:41][CH:42]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][C@H:14]([CH3:16])[N:13]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:12][C@H:11]2[CH3:25])=[O:9])=[C:4]([CH:3]=1)[CH2:28][O:29][C:47](=[O:48])[NH:46][S:43]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=1[CH3:49])(=[O:44])=[O:45]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2-(4-chloro-2-hydroxymethyl-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.050 g, 0.12 mmol) in dry toluene (2 mL) was added triethylamine (0.05 mL, 0.36 mmol) followed by o-toluenesulfonylisocyanate (0.05 mL, 0.36 mmol) and catalytic 4-dimethylaminopyridine. After 23 hours the reaction was warmed to 55° C. for 2 hours. After cooling the reaction was evaporated to dryness and the title compound purified by silica gel chromatography (0.074 g, LRMS: 618.1).

Workup

temperatureAfter cooling the reaction
customwas evaporated to dryness
customthe title compound purified by silica gel chromatography (0.074 g, LRMS: 618.1)

Sources & evidence

ORD record: ord-3c0eb05c8a254cc7ada9c39c6c9c73e0
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098212B2

Reaction notes

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