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tert-Butyl acetate → benzyl 3-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 470928
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HRID 470928 반응식
[OH:1][CH:2]([C:7]1[C:8]([CH3:34])=[N:9][C:10]2[CH2:11][CH2:12][N:13]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[CH2:14][C:15]=2[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[C:3]([O:5][CH3:6])=[O:4].C(O[C:39]([CH3:42])([CH3:41])[CH3:40])(=O)C>C(Cl)Cl>[C:39]([O:1][CH:2]([C:7]1[C:8]([CH3:34])=[N:9][C:10]2[CH2:11][CH2:12][N:13]([C:24]([O:26][CH2:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[CH2:14][C:15]=2[C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[C:3]([O:5][CH3:6])=[O:4])([CH3:42])([CH3:41])[CH3:40]
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참가 물질

4

반응물 2

HCID 10908tert-Butyl acetateHCID 86692201benzyl 3-(1-hydroxy-2-methoxy-2-oxoethyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate2회

생성물 1

HCID 86692202benzyl 3-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate수율 73.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of benzyl 3-(1-hydroxy-2-methoxy-2-oxoethyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (intermediate 11) (0.10 g, 0.217 mmol) in CH2Cl2 (3 ml) was added tert-butyl acetate (2.05 ml, 15.2 mmol) followed by HClO4 (0.056 ml, 0.651 mmol). The flask was sealed and stirred at room temperature for 2.5 h. The reaction was quenched with sat'd aq NaHCO3 (gas evolution). The organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by flash column chromatography (Biotage; 0%-30% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give benzyl 3-(1-(tert-butoxy)-2-methoxy-2-oxoethyl)-2-methyl-4-(p-tolyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (82.4 mg, 72% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.01-7.78 (m, 9H), 5.13 (s, 2H), 4.97 (s, 1H), 4.29-4.32 (m, 1H), 4.05-4.10 (m, 1H), 3.78-3.81 (m, 2H), 3.71 (s, 3H), 3.06 (bs, 2H), 2.64 (s, 3H), 2.45 (s, 3H) 0.99 (s, 9H). LCMS (M+H) calcd for C31H37N2O5: 517.27. found: 517.4.

후처리

  1. customThe flask was sealed
  2. customThe reaction was quenched with sat'd aq NaHCO3 (gas evolution)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography (Biotage; 0%-30% EtOAc/hexanes)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e1e2dac7a9684574be810775688814bb
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08629276B2

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