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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
ノート
印刷プレビュー

反応式

HRID 1481294 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-64b87fdc8e9b48239d5912f4bd06e57b
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409908B2

反応ノート

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