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Acetone → (Phenylmethyl) [5-[2-[4-(4-morpholinyl)phenyl]ethoxy] pentyl]carbamate

HRID 1084961
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HRID 1084961 반응식
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C[C:8](C)([CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:21][CH:20]=1)C(O)=O.C(N([CH2:37][CH3:38])CC)C.[N-:39]=[N+]=[N-].[Na+].[CH3:43][C:44]([CH3:46])=O>O>[N:25]1([C:22]2[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][O:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:8][NH:39][C:2](=[O:3])[O:4][CH2:5][C:6]3[CH:38]=[CH:37][CH:46]=[CH:44][CH:43]=3)=[CH:24][CH:23]=2)[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 180Acetone2회HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 200628192,2-Dimethyl-6-[2-[4-(4-morpholinyl)phenyl]ethoxy]hexanoic acid

생성물 1

HCID 53892071(Phenylmethyl) [5-[2-[4-(4-morpholinyl)phenyl]ethoxy] pentyl]carbamate

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

Ethyl chloroformate (3.29 g) in acetone (10 ml) was added dropwise to a solution of the product of stage (iii) (10.0 g) and triethylamine (3.0 g, 30 mmol) in acetone (100 ml) and water (10 ml) at 0°. The mixture was stirred at 0° for 40 min and sodium azide (2.0 g) in water (25 ml) was added dropwise. The resulting suspension was stirred at room temperature for 45 min, diluted with water (200 ml) and extracted with T (2×200 ml). The dried (Na2SO4) extract was heated at 75°-80° for 2.5 h and evaporated. The residue was treated with benzyl alcohol (20 ml), heated at 75°-80° for 60 h and benzyl alcohol was removed by distillation (~1 mmHg). The resulting oil was purified on a column of silica (Merck 9385) eluted with ER-CX (1:2) to give the title compound, as a yellow oil (4.74 g). T.l.c. ER-CX (1:2) Rf 0.13.

후처리

  1. stirringThe resulting suspension was stirred at room temperature for 45 min
  2. extractionextracted with T (2×200 ml)
  3. dry with materialThe dried (Na2SO4)
  4. extractionextract
  5. temperaturewas heated at 75°-80° for 2.5 h
  6. customevaporated
  7. additionThe residue was treated with benzyl alcohol (20 ml)
  8. temperatureheated at 75°-80° for 60 h
  9. custombenzyl alcohol was removed by distillation (~1 mmHg)
  10. customThe resulting oil was purified on a column of silica (Merck 9385)
  11. washeluted with ER-CX (1:2)

출처 및 근거

ORD 기록
ord-c4f713ebfa244341a18f3f5e2d03cf86
출처 데이터셋
uspto-grants-1991_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05006556

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