Tributylphosphine → 6-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-{2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]thiazol-5-yl}-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

HRID 1096871

反応式

HRID 1096871 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[CH:5]=[C:4]([CH3:10])[CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:25][CH:24]2[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:20]([CH2:21][C:22]([C:50]3[S:54][C:53]([O:55][CH2:56][CH2:57]O)=[N:52][CH:51]=3)=[C:23]2[C:34](=[O:49])[N:35]([CH:46]2[CH2:48][CH2:47]2)[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[C:38]=2[CH3:45])[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].P(CCCC)(CCCC)CCCC>C1(C)C=CC=CC=1.CCOCC>[C:11]([O:15][C:16]([N:18]1[CH2:25][CH:24]2[N:26]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH:20]([CH2:21][C:22]([C:50]3[S:54][C:53]([O:55][CH2:56][CH2:57][O:8][C:7]4[C:2]([Cl:1])=[CH:3][C:4]([CH3:10])=[CH:5][C:6]=4[Cl:9])=[N:52][CH:51]=3)=[C:23]2[C:34](=[O:49])[N:35]([CH:46]2[CH2:47][CH2:48]2)[CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([O:43][CH3:44])[C:38]=2[CH3:45])[CH2:19]1)=[O:17])([CH3:12])([CH3:13])[CH3:14]

参加物

6

反応物 3

HCID 13831TributylphosphineHCID 170772,6-Dichloro-4-methylphenolHCID 685707976-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-[2-(2-hydroxyethoxy)thiazol-5-yl]-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester

生成物 1

HCID 685710656-[Cyclopropyl-(3-methoxy-2-methylbenzyl)carbamoyl]-7-{2-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]thiazol-5-yl}-3,9-diazabicyclo[3.3.1]non-6-ene-3,9-dicarboxylic acid di-tert-butyl ester収率 76%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

A sol. of 2,6-dichloro-p-cresol (0.55 mmol; 97 mg) in toluene (4.8 mL) was treated with compound E9 (0.37 mmol; 250 mg) followed by azodicarboxylic dipiperidide (0.73 mmol; 184 mg) and PBu3 (1.28 mmol; 0.27 mL). The reaction mixture was stirred at 80° C. After 1 h, the reaction mixture was allowed to cool to rt, diluted with Et2O (50 mL), filtrated, and the filtrate was washed with NaOH 1M (50 mL) and brine (50 mL). The org. extract was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 30:70) yielded the title compound (0.23 g, 76%). LC-MS: tR=1.25 min; ES+: 843.29.

後処理

  1. temperatureto cool to rt
  2. filtrationfiltrated
  3. washthe filtrate was washed with NaOH 1M (50 mL) and brine (50 mL)
  4. extractionextract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (EtOAc/heptane 30:70)

出典と根拠

ORDレコード
ord-8113673050884606b0e167c280617300
出典データセット
uspto-grants-2012_03
特許番号
US08138340B2

関連ノート

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