Sodium Bicarbonate → methyl 2-(((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate

HRID 41796

반응식

HRID 41796 반응식
Cl.CO.C(OC([N:11]([C:39]1[C:48]([N+:49]([O-:51])=[O:50])=[CH:47][CH:46]=[CH:45][C:40]=1[C:41]([O:43][CH3:44])=[O:42])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[N:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:28]=[N:27][N:26]=2)=[CH:15][CH:14]=1)=O)(C)(C)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:29]2[C:25]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[C:16]3[CH:15]=[CH:14][C:13]([CH2:12][NH:11][C:39]4[C:48]([N+:49]([O-:51])=[O:50])=[CH:47][CH:46]=[CH:45][C:40]=4[C:41]([O:43][CH3:44])=[O:42])=[CH:18][CH:17]=3)=[N:26][N:27]=[N:28]2)=[CH:32][CH:33]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 70664089methyl 2-((tert-butoxycarbonyl)((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate2회

생성물 1

HCID 69916865methyl 2-(((2'-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-nitrobenzoate수율 101%

시약·촉매·용매 1

HCID 21584019Toluene ethylacetate용매

반응 조건

온도
3 °C

실험 절차

To hydrogen chloride-methanol (30%; 26.9 g, net 8.08 g, 222 mmol) was added methyl 2-(N-tert-butoxycarbonyl-N-{(2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl)methyl}amino)-3-nitrobenzoate (compound 20a, 5.00 g, 7.68 mmol) over 13 min by four portions at 4-5° C. The mixture was stirred at about 3° C. for 2 hr, and warmed to 9° C. over 1 hr. The reaction was monitored by TLC (eluent: toluene/ethyl acetate (2:1)). The reaction mixture was cooled to 3° C., and saturated aqueous sodium hydrogen carbonate solution (180 mL) was added dropwise thereto at 30° C. or lower. The mixture was extracted twice with ethyl acetate (450 mL, 250 mL), and the combined organic layers were washed with saturated brine (200 mL), dried over magnesium sulfate (10 g), and concentrated under reduced pressure at 40° C. or lower. To the concentrate was added chloroform, and the solvent was evaporated under reduced pressure in a bath at 40° C. to give methyl 2-[({2′-[1-(p-methoxybenzyl)-1H-tetrazol-5-yl]biphenyl-4-yl}methyl)amino]-3-nitrobenzoate (compound 21a, 4.27 g, 101%) as a yellowish brown amorphous solid.

후처리

  1. temperaturewarmed to 9° C. over 1 hr
  2. temperatureThe reaction mixture was cooled to 3° C.
  3. customat 30° C.
  4. extractionThe mixture was extracted twice with ethyl acetate (450 mL, 250 mL)
  5. washthe combined organic layers were washed with saturated brine (200 mL)
  6. dry with materialdried over magnesium sulfate (10 g)
  7. concentrationconcentrated under reduced pressure at 40° C.
  8. additionTo the concentrate was added chloroform
  9. customthe solvent was evaporated under reduced pressure in a bath at 40° C.

출처 및 근거

ORD 기록
ord-17df946ec69949f6b7f38cfc46566a8e
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530506B2

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