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Methyl Isocyanate → 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-(N-methylcarbamoyloxy)pregn-5-en-3beta-yl acetate

HRID 1196321
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HRID 1196321 반응식
[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([OH:35])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][O:18]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2].[CH3:36][N:37]=[C:38]=[O:39].C(OCC)(=O)C.CCCCCC>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[C@@H:31]2[O:32][C@@H:30]2[C@@:29]2([CH3:33])[C:7](=[CH:8][C@@H:9]([O:35][C:38](=[O:39])[NH:37][CH3:36])[C@@H:10]3[C@@H:28]2[CH2:27][CH2:26][C@@:25]2([CH3:34])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[CH:15]([CH:17]2[O:18][CH2:19][C:20]([CH3:23])([CH3:24])[CH2:21][O:22]2)[CH3:16])[CH2:6]1)(=[O:3])[CH3:2]
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참가 물질

6

반응물 3

HCID 12228Methyl IsocyanateHCID 21226206Ethyl acetate hexaneHCID 8674580220-(5,5-Dimethyl-1,3-dioxan-2-yl)-1alpha, 2alpha-epoxy-7alpha-hydroxypregna-5-en-3beta-yl acetate

생성물 1

HCID 8846371220-(5,5-dimethyl-1,3-dioxan-2-yl)-1alpha,2alpha-epoxy-7alpha-(N-methylcarbamoyloxy)pregn-5-en-3beta-yl acetate수율 65%

시약·촉매·용매 2

HCID 1049
Pyridine
촉매
HCID 1140Toluene용매

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온도
60 °C

실험 절차

In 5 ml of toluene was dissolved 49.0 mg (0.1 mmole) of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-hydroxypregn-5-en-3β-yl acetate, followed by addition of one drop of pyridine. Then, 0.1 ml (1.7 mmoles) of methyl isocyanate was added at a temperature of 0° C. and the mixture was stirred at a temperature of 60° C. for 30 minutes. The reaction mixture thus obtained was cooled to room temperature, poured in ice-water, and extracted 3 times with 20 ml portions of methylene chloride. The extracts are pooled, washed successively with water and aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. Finally the residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1:10, v/v) to recover 35 mg of 20-(5,5-dimethyl-1,3-dioxan-2-yl)-1α,2α-epoxy-7α-(N-methylcarbamoyloxy)pregn-5-en-3β-yl acetate (yield: 65%).

후처리

  1. customThe reaction mixture thus obtained
  2. temperaturewas cooled to room temperature
  3. extractionextracted 3 times with 20 ml portions of methylene chloride
  4. washwashed successively with water and aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customFinally the residue was purified by silica gel chromatography (eluent

출처 및 근거

ORD 기록
ord-394d19debeef442380d961d8c53d8423
출처 데이터셋
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05112998

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