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Tert-Butylamine → 1-Fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide

HRID 257334
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HRID 257334 반응식
[F:1][C:2]1([C:9]([OH:11])=O)[CH2:6][CH2:5][CH2:4][CH:3]1[O:7][CH3:8].C(N(CC)CC)C.C(Cl)(=O)OCC.[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26]>O1CCCC1.O>[C:25]([NH:29][C:9]([C:2]1([F:1])[CH2:6][CH2:5][CH2:4][CH:3]1[O:7][CH3:8])=[O:11])([CH3:28])([CH3:27])[CH3:26]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 197831041-Fluoro-2-methoxy-1-cyclopentanecarboxylic acid

생성물 1

HCID 867473651-Fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide수율 55%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

0.4 g (2.7 mmol) of 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid in cis form (compound number 12a) disclosed in Example 12 and 0.27 g (2.7 mmol) of triethylamine were dissolved in 10 ml of tetrahydrofuran, and the solution was cooled to 0° C. 0.29 g (2.7 mmol) of ethyl chlorocarbonate was added dropwise, the mixture was stirred at 0° C. for 1 hour, 0.24 g (3.2 mmol) of tertiary butylamine was add, and the mixture was further stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ether, and the extract was washed with saturated saline. The ether layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away to obtain 0.3 g (yield: 55%) of the objective 1-fluoro-2-methoxy-1-cyclopentanecarboxylic acid tertiary butylamide in cis form (compound number 29a).

후처리

  1. stirringthe mixture was further stirred at room temperature for 1 hour
  2. extractionextracted with ether
  3. washthe extract was washed with saturated saline
  4. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away

출처 및 근거

ORD 기록
ord-a2b8a946512e41d99209bb539af690a5
출처 데이터셋
uspto-grants-1993_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05262385

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