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

HRID 1443493ノート

反応式

HRID 1443493 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-30b01fcfee694c948fa03e1fc3c430ec
出典データセット
uspto-grants-2010_02
特許番号
US07659245B2

反応ノート

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