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Potassium Phosphate, Tribasic → tert-Butyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}pyridin-3-yl)carbamate

HRID 1481294
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HRID 1481294 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH:10]=[CH2:11])[CH:3]=1.[C:20]([O:24][C:25]([NH:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][C:33]=1B(O)O)=[O:26])([CH3:23])([CH3:22])[CH3:21].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[C:15]([O:14][C:13]([NH:12][C@H:8]([C:4]1[CH:3]=[C:2]([C:33]2[CH:32]=[CH:31][N:30]=[CH:29][C:28]=2[NH:27][C:25](=[O:26])[O:24][C:20]([CH3:22])([CH3:21])[CH3:23])[CH:7]=[CH:6][N:5]=1)[CH2:9][CH:10]=[CH2:11])=[O:19])([CH3:18])([CH3:17])[CH3:16]
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참가 물질

5

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 15366412(3-((tert-Butoxycarbonyl)amino)pyridin-4-yl)boronic acidHCID 66744734Carbamic acid, N-[(1S)-1-(4-chloro-2-pyridinyl)-3-buten-1-yl]-, 1,1-dimethylethyl ester

생성물 1

HCID 131736624tert-Butyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}pyridin-3-yl)carbamate수율 40%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
75 °C

실험 절차

To 1C (1.080 g, 3.82 mmol) and (3-((tert-butoxycarbonyl)amino)pyridin-4-yl)boronic acid (1 g, 4.20 mmol) in a sealable flask was added THF (19.09 ml), potassium phosphate tribasic (5.09 ml, 15.28 mmol) and degassed with Ar. (DtBPF)PdCl2 (0.249 g, 0.382 mmol) was added, degassed further. The reaction mixture was heated at 75° C. for overnight. Then, the mixture was washed with water and extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, concentrated and purified by ISCO to yield 72A as brown solid (670 mg, 40%). 1H NMR (500 MHz, METHANOL-d4) δ 8.65 (br. s., 1H), 8.62-8.57 (m, 1H), 8.46 (d, J=5.0 Hz, 1H), 7.46 (s, 1H), 7.41 (d, J=5.2 Hz, 1H), 7.39 (m, 1H), 5.86-5.75 (m, 1H), 5.15-5.03 (m, 2H), 4.81-4.75 (m, 1H), 2.68-2.57 (m, 1H), 2.55-2.46 (m, 1H), 1.46-1.27 (m, 18H).

후처리

  1. customdegassed with Ar
  2. customdegassed further
  3. washThen, the mixture was washed with water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by ISCO

출처 및 근거

ORD 기록
ord-64b87fdc8e9b48239d5912f4bd06e57b
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409908B2

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