반응 #49224

반응 방정식

(2R,4R)-tert-butyl 2-((1S,2S)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)-2-(3-(methoxycarbonyl)-5-methylbenzamido)propyl)-4-propoxypyrrolidine-1-carboxylate

LiOH

( 5 )

(2R,4R)-tert-butyl 2-((1S,2S)-2-(3,5-difluorobenzyl)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-1-hydroxy-3-oxopropyl)-4-(allyloxy)pyrrolidine 1-carboxylate

3-(((1S,2S)-1-((2R,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidin-2-yl)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)propan-2-yl)carbamoyl)-5-methylbenzoic acid

→

title compound

3-(dipropylcarbamoyl)benzoic acid

용매

THF

H2O

Ethyl ether

MeOH

반응 조건

후처리

1. 1
   workup.STIRRINGstirred for another 2 h at rt
2. 2
   세척washed with 1N HCl, H2O
3. 3
   건조dried (Na2SO4)
4. 4
   농축concentrated in vacuo

실험 절차

Step G (5): Preparation of 3-(((1S,2S)-1-((2R,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidin-2-yl)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)propan-2-yl)carbamoyl)-5-methylbenzoic acid. To a solution of (2R,4R)-tert-butyl 2-((1S,2S)-1-(tert-butyldimethylsilyloxy)-3-(3,5-difluorophenyl)-2-(3-(methoxycarbonyl)-5-methylbenzamido)propyl)-4-propoxypyrrolidine-1-carboxylate (Step G (4), 110 mg, 0.16 mmol) in THF (2 mL) was added a solution of LiOH (18 mg, 0.8 mmol) in H2O (0.4 mL). This reaction mixture was stirred at rt for 2 h. MeOH (2 mL) was added to the reaction mixture and stirred for another 2 h at rt. Ethyl ether (100 mL) was added to the mixture and washed with 1N HCl, H2O, dried (Na2SO4), and concentrated in vacuo to give 105 mg of the title compound: 1H NMR (CDCl3, 500 MHz) δ ppm 0.05 (3H, s), 0.10 (3H, s), 0.93 (3H, m), 0.97 (9H, s), 1.47 (9H, s), 1.58 (2H, m), 2.26 (1H, m), 2.39 (3H, s), 2.47-2.52 (1H, m), 2.61 (1H, m), 3.07 (1H, m), 3.27 (1H, m), 3.37 (1H, dt, J=5, 10 Hz), 3.47 (1H, dt, J=5, 10 Hz), 3.86 (1H, dd, J=5, 10 Hz), 3.97 (1H, m), 4.12 (1H, m), 4.36 (1H, m), 4.50 (1H, m), 6.47 (1H, m), 6.89 (1H, s), 6.90 (1H, s), 7.90 (1H, s), 7.95 (1H, s), 8.26 (1H, d, J=10 Hz), 8.54 (1H, s). MS (ESI) (M−H)− 689.49.

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