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Sodium hydride → 6-(2-methylallyl)-6-phenyl-3-(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)-1,3-oxazinan-2-one

HRID 1422650
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HRID 1422650 반응식
[OH:1][C:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([CH2:24][C:25]([CH3:27])=[CH2:26])[CH2:3][CH2:4][N:5]([C:10]([C:13]1[N:14]=[N:15][N:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:17]=1)([CH3:12])[CH3:11])[C:6](=O)[O:7]C.[H-].[Na+]>C1COCC1.Cl.CO>[CH3:27][C:25](=[CH2:26])[CH2:24][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:1][C:6](=[O:7])[N:5]([C:10]([C:13]2[N:14]=[N:15][N:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:17]=2)([CH3:11])[CH3:12])[CH2:4][CH2:3]1
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참가 물질

6

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HCID 24758Sodium hydrideHCID 68160533methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate

생성물 1

HCID 509057376-(2-methylallyl)-6-phenyl-3-(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)-1,3-oxazinan-2-one수율 67.4%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of methyl 3-hydroxy-5-methyl-3-phenylhex-5-enyl(2-(1-phenyl-1H-1,2,3-triazol-4-yl)propan-2-yl)carbamate (14 mg, 0.031 mmol) in dry THF (1 mL) was added 60% NaH in oil (10 mg, 0.25 mmol). The mixture was heated at 50 C in an oil bath for 1.5 h, cooled, diluted with 5% aq HCl (0.5 mL) and MeOH (0.5 mL) and purified by prep HPLC to afford the title compound (8.7 mg, 67%) as an oil. LC-MS Method 1 tR=1.90 min, m/z=417; 1H NMR (CDCl3) 1.58 (s, 3H), 1.76 (s, 6H), 2.25 (m, 1H), 2.36 (m, 1H), 2.56 (dd, 2H), 3.03 (m, 1H), 3.52 (m, 1H), 4.58 (s, 1H), 4.81 (s, 1H), 7.25-7.80 (11H).

후처리

  1. temperatureThe mixture was heated at 50 C in an oil bath for 1.5 h
  2. temperaturecooled
  3. custompurified by prep HPLC

출처 및 근거

ORD 기록
ord-9560ee898c914b6d86c0b5dac4920378
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927539B2

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