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Cesium carbonate → Tert-butyl 1-(isopropoxycarbonyl)-4-oxo-3-o-tolylpentylcarbamate

HRID 706382
ノート
印刷プレビュー

反応式

HRID 706382 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16]OS(C)(=O)=O)[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]1([CH3:32])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][C:29](=[O:31])[CH3:30].C([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1.CS(C)=O>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][CH:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH3:32])[C:29](=[O:31])[CH3:30])[C:10]([O:12][CH:13]([CH3:14])[CH3:15])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 27341091-(2-Methylphenyl)propan-2-oneHCID 89815000isopropyl N-(tert-butoxycarbonyl)-O-(methylsulfonyl)serinate

生成物 1

HCID 89814785Tert-butyl 1-(isopropoxycarbonyl)-4-oxo-3-o-tolylpentylcarbamate収率 65.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒2 回
HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of 2 (181.2 g, 0.557 mol) in THF (1 L) was added TEA (84.6 g, 0.836 mol) in portions at 15-20° C. The mixture was stirred for 30 h. After the reaction was complete, the solution was concentrated to give crude 7. To a solution of 35 (82.5 g, 0.557 mol) and Cs2CO3 (91 g, 0.279 mol) in DMSO (1 L) was added slowly crude 7 in DMSO (500 mL) over 30 min at 15-20° C. The mixture was stirred for 1 h. After the reaction was complete, the mixture was partitioned with water and MTBE (5 L), and extracted with MTBE twice. The combined organic layer was dried over Na2SO4 and concentrated. The crude residual was further purified by flash chromatography on silica gel (5-10% EtOAc/PE) to give 36 (138 g, 65% yield).

後処理

  1. concentrationthe solution was concentrated
  2. customto give crude 7
  3. stirringThe mixture was stirred for 1 h
  4. customthe mixture was partitioned with water and MTBE (5 L)
  5. extractionextracted with MTBE twice
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude residual was further purified by flash chromatography on silica gel (5-10% EtOAc/PE)

出典と根拠

ORDレコード
ord-1e1c02338f0f4433b4880d4b3b6b275f
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09174989B2

反応ノート

読み込み中…

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