Water → HCID 57941331, compound

HRID 1437880Notes

Reaction equation

HRID 1437880 reaction equation
C(N(CC)CC)C.[CH3:8][C@@:9]12[C:15]([CH3:17])([CH3:16])[C@@H:12]([CH2:13][CH2:14]1)[CH:11]([C:18](Cl)=[O:19])[C:10]2=[O:21].[C:22]([O:26][C:27]([NH:29][NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])=[O:28])([CH3:25])([CH3:24])[CH3:23].O>ClCCl>[C:22]([O:26][C:27]([NH:29][N:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[F:37])[C:18]([CH:11]1[C:10](=[O:21])[C@:9]2([CH3:8])[C:15]([CH3:17])([CH3:16])[C@H:12]1[CH2:13][CH2:14]2)=[O:19])=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 579413791,1-Dimethylethyl 2-(2-fluorophenyl)hydrazinecarboxylate2×HCID 57941380HCID 57941380, compound2×

Product 1

HCID 57941331HCID 57941331, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3 mL, 21.5 mmol) was added dropwise to a cooled (0° C.) solution of (1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl chloride (Intermediate 25; 1.50 g, 7.0 mmol) in dichloromethane (18 mL), yielding a thick suspension. This was stirred for 3 min and then N′-(2-fluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (Intermediate 29; 1.20 g, 5.3 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature and stir for 2.5 h. The mixture was added to water (50 mL) and extracted with dichloromethane (3×40 mL). The combined organic layers were washed with brine (30 mL), dried (magnesium sulfate), filtered, evaporated, and dried under high vacuum at room temperature for 30 min to give N′-(2-fluoro-phenyl)-N′-((1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl)-hydrazinecarboxylic acid tert-butyl ester (2.67 g, 124% of the expected amount) as an orange foam. This was used directly in the next step without further purification.

Workup

  1. customyielding a thick suspension
  2. stirringstir for 2.5 h
  3. extractionextracted with dichloromethane (3×40 mL)
  4. washThe combined organic layers were washed with brine (30 mL)
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customdried under high vacuum at room temperature for 30 min

Sources & evidence

ORD record
ord-9ac3bdb9afa04c3e80422d1734677db4
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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