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Triethylamine → [3-Chloro-5-(tert-butyldimethylsilyloxy)phenyl]-n-cyclopentyl-n-prop-2-enylcarboxamide

HRID 988088
ノート
印刷プレビュー

反応式

HRID 988088 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:10]=1)[C:5]([OH:7])=O.C(N(CC)CC)C.O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.[CH2:41]([NH:44][CH:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)[CH:42]=[CH2:43]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N:44]([CH:45]2[CH2:49][CH2:48][CH2:47][CH2:46]2)[CH2:41][CH:42]=[CH2:43])=[O:7])[CH:8]=[C:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:10]=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 8471TriethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 5062349N-(prop-2-en-1-yl)cyclopentanamineHCID 180074783-Chloro-5-(tert-butyldimethylsilyloxy)benzoic acid

生成物 1

HCID 131724100[3-Chloro-5-(tert-butyldimethylsilyloxy)phenyl]-n-cyclopentyl-n-prop-2-enylcarboxamide収率 99.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3-chloro-5-(tert-butyldimethylsilyloxy)benzoic acid (17.5 g, 60 mmol), as prepared in the preceding step, and CH2Cl2 (250 mL) were added triethylamine (33.8 mL, 0.24 mol) and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (17.0 g, 66 mmol). The resulting mixture was stirred for 5 min, then N-allylcyclopentylamine (9.8 mL, 66 mmol) was added. After 1 h, the solution was filtered. The filtrate was washed with 10% aqueous HCl (100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL). The organic layer was dried over anhydrous MgSO4, concentrated in vacuo, and flash chromatographed to provide the title compound as a colorless oil (23.5 g, 97%). 1H NMR (CDCl3) δ 6.95 (s, 1H), 6.84 (s, 1H), 6.71 (s, 1H), 5.93 (br s, 1H), 5.16 (d, 2H), 3.95 (br s, 3H), 1.4-1.9 (m, 8H), 0.97 (s, 9H), 0.20 (s, 6H). Mass spectrum (CI) calcd. for C21H32NO2SiCl: 394 (M+H). Found: 394.

後処理

  1. waitAfter 1 h
  2. filtrationthe solution was filtered
  3. washThe filtrate was washed with 10% aqueous HCl (100 mL), saturated aqueous NaHCO3 (100 mL), and brine (100 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated in vacuo, and flash
  6. customchromatographed

出典と根拠

ORDレコード
ord-63838f7432fe4393adea5a50beefd3b1
出典データセット
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06635637B2

反応ノート

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