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Diisopropylethylamine → (1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylate

HRID 926005
ノート
印刷プレビュー

反応式

HRID 926005 の反応式
[C:1]([O:5][C:6]([C@@H:8]1[CH2:13][C@H:12]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10][C@H:9]1[C:32](O)=[O:33])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:68][NH:69][CH2:70][CH2:71][CH2:72][CH2:73][CH:74]=[CH2:75].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Si:15]([O:14][C@H:12]1[CH2:13][C@@H:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C@H:9]([C:32](=[O:33])[N:69]([CH2:70][CH2:71][CH2:72][CH2:73][CH:74]=[CH2:75])[CH3:68])[CH2:10][CH2:11]1)([C:28]([CH3:29])([CH3:31])[CH3:30])([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46737741N-methylhex-5-en-1-amine 4-methylbenzenesulfonateHCID 58282618(1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid

生成物 1

HCID 58282736
(1R,2R,5R)-tert-butyl 5-(tert-butyldiphenylsilyloxy)-2-(hex-5-enyl(methyl)carbamoyl)cyclohexanecarboxylate
収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a cold solution of compound 38 (1.80 mmol), TBTU (2.17 mmol), and N-methylhex-5-en-1-amine tosylate salt 31a (2.17 mmol) in DMF (100 mL) was added diisopropyl ethyl amine (5.4 mmol) dropwise under nitrogen at 0° C. The reaction mixture was stirred overnight at room temperature, then quenched with water and extracted with diethyl ether. The organic layer was washed with brine, then dried on magnesium sulphate, concentrated under reduced pressure, and purified by chromatography on silica gel to yield compound 39 as a beige solid in 85% yield. MS (ESI, EI+): m/z=578 (MH+).

後処理

  1. customquenched with water
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with brine
  4. customdried on magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography on silica gel

出典と根拠

ORDレコード
ord-10de6d2e467a4f4fbed409be22380b0b
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09284307B2

反応ノート

読み込み中…

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