Triethylamine → HCID 67352364, 화합물

HRID 1669497노트

반응식

HRID 1669497 반응식
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[O:22]([C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:32]2[CH:33]=[CH:34][C:29]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:30][CH:31]=2)=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27343774-Phenoxyphenylboronic acidHCID 7016055Boc-D-Tyr-OMe

생성물 1

HCID 67352364HCID 67352364, 화합물수율 47%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of Boc-D-Tyrosine-Methyl ester (0.150 g, 0.508 mmol), 4-Phenoxyphenyl-boronic acid (0.109 g, 0.508 mmol), and triethylamine (0.355 mL, 2.539 mmol) in anhydrous dichloromethane (DCM) (12.5 mL) at room temperature under an atmosphere of nitrogen was added copper (II) acetate (0.070 g, 0.508 mmol), and the resulting mixture was stirred at room temperature for about 18 h. The reaction mixture was washed with 20 mL of water and 20 mL of DCM and filtered. The DCM layer was then extracted. The aqueous layer was re-extracted with DCM (2×15 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and the solvent was removed in vacuo to obtain the crude mixture, which was purified by of silica gel flash chromatography, using ethyl acetate (EtOAc)/hexane (gradient system), to obtain the product (110 mg, 47%): 1H NMR (400 MHz, CDCL3): δ 1.42 (s, 9H), 2.98-3.09 (m, 2H), 3.71 (d, J=5.2 Hz), 4.55-4.58 (m, 1H), 4.98-5.01 (m, 1H), 6.75 (d, 1H, J=8.4 Hz), 6.91-7.02 (m, 6H), 7.07-7.11 (m, 3H), 7.31-7.35 (m, 2H); MS: m/z 364 (MH)+ & no -boc group, m/z 464 (MH)+.

후처리

  1. washThe reaction mixture was washed with 20 mL of water and 20 mL of DCM
  2. filtrationfiltered
  3. extractionThe DCM layer was then extracted
  4. extractionThe aqueous layer was re-extracted with DCM (2×15 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto obtain the crude mixture, which
  9. customwas purified by of silica gel flash chromatography

출처 및 근거

ORD 기록
ord-a2964b173ed348e4b0c8a5d3a3fa8f93
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989480B2

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