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

HRID 1443493Notes

Reaction equation

HRID 1443493 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-30b01fcfee694c948fa03e1fc3c430ec
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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