Diisopropylethylamine → 1-{[2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1443493노트

반응식

HRID 1443493 반응식
Cl.[CH2:2]([O:4][C:5]([C:7]1([NH2:12])[CH2:9][CH:8]1[CH:10]=[CH2:11])=[O:6])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:37]([N:43]([CH3:55])[C:44]([CH:46]1[CH2:50][CH:49]([OH:51])[CH2:48][CH:47]1[C:52](O)=[O:53])=[O:45])[CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:2]([O:4][C:5]([C:7]1([NH:12][C:52]([CH:47]2[CH2:48][CH:49]([OH:51])[CH2:50][CH:46]2[C:44](=[O:45])[N:43]([CH2:37][CH2:38][CH2:39][CH2:40][CH:41]=[CH2:42])[CH3:55])=[O:53])[CH2:9][CH:8]1[CH:10]=[CH2:11])=[O:6])[CH3:3]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 53419329Ethyl 1-amino-2-vinylcyclopropane-1-carboxylate hydrochlorideHCID 684256202-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid

생성물 1

HCID 668706071-{[2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester수율 60%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1-(Amino)-2-(vinyl)cyclopropanecarboxylic acid ethyl ester hydrochloride (4.92 g, 31.7 mmol) and HATU (12.6 g, 33.2 mmol) were added to the acid (142) (8.14 g, 30.2 mmol). The mixture was cooled in an ice bath under argon, and then DMF (100 mL) and DIPEA (12.5 mL, 11.5 mmol) were added. After 30 min at 0° C., the solution was stirred at room temperature for an additional 3 h. Then, the reaction mixture was partitioned between EtOAc and water, washed successively with 0.5 N HCl (20 mL) and saturated NaCl (2×20 mL), and dried (Na2SO4). Purification by flash chromatography (EtOAc/CH2Cl2/Petroleum ether, 1:1:1) afforded the title compound (7.41, g 60%) as a colorless oil, m/z=407 (M+H)+.

후처리

  1. temperatureThe mixture was cooled in an ice bath under argon
  2. customThen, the reaction mixture was partitioned between EtOAc and water
  3. washwashed successively with 0.5 N HCl (20 mL) and saturated NaCl (2×20 mL)
  4. dry with materialdried (Na2SO4)
  5. customPurification by flash chromatography (EtOAc/CH2Cl2/Petroleum ether, 1:1:1)

출처 및 근거

ORD 기록
ord-30b01fcfee694c948fa03e1fc3c430ec
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659245B2

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