반응 #42595

반응 방정식

acid

4-[(methylsulfonyl)methyl]cyclohexanecarboxylic acid

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol

HATU

N,N-diisopropylethylamine

→

title compound

수율 22.4%

N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-4-[(methylsulfonyl)methyl]cyclohexanecarboxamide

수율 22.4%

용매

methylene chloride

반응 조건

후처리

1. 1
   기타The reaction mixture was partitioned between methylene chloride and water
2. 2
   세척The organic layer was washed with water
3. 3
   건조dried (sodium sulfate)
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타to afford a crude oil
7. 7
   기타Purification by flash column chromatography (silica, gradient 95:5 to 92:8 methylene chloride/methanol)

실험 절차

To a stirred solution of acid from step 6 (100 mg, 0.5 mmol), (2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-ethylbenzyl)amino]butan-2-ol (190 mg, 0.5 mmol), and HATU (175 mg, 0.5 mmol) in methylene chloride (5 mL) was added N,N-diisopropylethylamine (280 μL, 1.6 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between methylene chloride and water. The organic layer was washed with water, dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, gradient 95:5 to 92:8 methylene chloride/methanol) provided the title compound (60 mg): mp 45-50° C.; ESI MS m/z 537 [M+H]+.

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