Sodium Carbonate → Methyl 4-(4-{[(4-tert-Butylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate

HRID 931429

反応式

HRID 931429 の反応式
[O-]S([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[Na+].[Na+].[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].Cl[CH2:28][C:29]1[N:30]=[C:31]([C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=2)[O:32][C:33]=1[CH3:34]>O.CCO>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH2:28][C:29]2[N:30]=[C:31]([C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=3)[O:32][C:33]=2[CH3:34])(=[O:25])=[O:24])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 23076573Methyl 4-(4-(chloromethyl)-5-methyloxazol-2-yl)benzoate

生成物 1

HCID 68278317Methyl 4-(4-{[(4-tert-Butylphenyl)sulfonyl]methyl}-5-methyl-1,3-oxazol-2-yl)benzoate収率 26.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒3 回

反応条件

温度
100 °C

実験手順

A solution of Na2SO3 (126 mg, 1.0 mmol) and Na2CO3 (106 mg, 1.0 mmol) in water (2 mL) was added to a suspension of 4-tert-butylbenzenesulfonyl chloride (233 mg, 1.0 mmol) in water (5 mL) and the mixture was stirred at 100° C. for 2 h. A solution of chloride 2 (268 mg, 1.0 mmol) in EtOH (5 mL) was added and the mixture stirred at 100° C. for 16 h. The mixture was cooled and diluted with water (40 mL) and stirred for 15 min. The precipitate was filtered, washed with water (5 mL). The residue purified by column chromatography, eluting with a gradient (20-50%) of EtOAc/pet. ether, to give benzoate 22 (112 mg, 26%) as a white powder: mp (EtOAc) 190-192° C.; 1H NMR (CDCl3) δ 8.05 (ddd, J=8.6, 1.8, 1.5 Hz, 2H, H-2, H-6), 7.89 (ddd, J=8.6, 1.8, 1.5 Hz, 2H, H-3, H-5), 7.71 (ddd, J=8.6, 2.2, 1.8 Hz, 2H, H-2′, H-6′), 7.51 (ddd, J=8.6, 2.2, 1.8 Hz, 2H, H-3′, H-5′), 4.30 (s, 2H, CH2SO2), 3.94 (s, 3H, OCH3), 2.32 (s, 3H, CH3), 1.33 [s, 9H, C(CH3)3]; MS m/z 428.5 (MH+, 100%). Anal. calcd for C23H25NO5S: C, 64.62; H, 5.89; N, 3.28. Found: C, 64.70; H, 5.94; N, 3.25%.

後処理

  1. stirringthe mixture stirred at 100° C. for 16 h
  2. temperatureThe mixture was cooled
  3. stirringstirred for 15 min
  4. filtrationThe precipitate was filtered
  5. washwashed with water (5 mL)
  6. customThe residue purified by column chromatography
  7. washeluting with a gradient (20-50%) of EtOAc/pet. ether

出典と根拠

ORDレコード
ord-bb13505d50a347c89092de3c8ac76ee7
出典データセット
uspto-grants-2016_03
特許番号
US09296732B2

関連ノート

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