Sodium Hydroxide → HCID 68182595, compound

HRID 1623888Notes

Reaction equation

HRID 1623888 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH2:8][C@H:9]3[CH2:22][C@H:10]3[C:11]=2[N:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[N:13]=1)=[O:5])C.[OH-].[Na+]>CO.C1COCC1>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[N:12]1[C:11]2[C@@H:10]3[CH2:22][C@@H:9]3[CH2:8][C:7]=2[C:6]([C:4]([OH:5])=[O:3])=[N:13]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68182446(1aR,5aR)-2-(2,4-difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester

Product 1

HCID 68182595HCID 68182595, compoundYield 98.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of (1aR,5aR)-2-(2,4-difluoro-phenyl)-1a,2,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carboxylic acid ethyl ester (17.4 g, 57.2 mmol) in methanol (100 mL) and THF (100 mL) was added a 2.0 M aqueous solution of sodium hydroxide (86 mL, 172 mmol). The resulting orange solution was stirred at 23° C. for 3 h. The organic solvents were removed under reduced pressure. The remaining aqueous solution was diluted to 150 mL with water and then acidified to pH 2 by addition of 6 M HCl while stirring vigorously. The precipitate was collected by filtration, rinsed with water, and then dried under reduced pressure to give the title compound as a tan solid (15.62 g). LCMS m/z=277.3 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.41 (td, J=4.6, 3.4 Hz, 1H), 1.15 (td, J=7.8, 4.7 Hz, 1H), 2.16-2.21 (m, 1H), 2.23-2.29 (m, 1H), 2.76 (d, J=16.2 Hz, 1H), 2.90 (dd, J=16.4, 6.2 Hz, 1H), 7.27-7.32 (m, 1H), 7.56-7.62 (m, 1H), 7.75 (td, J=9.0, 5.9 Hz, 1H), 12.93 (bs, 1H).

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionThe remaining aqueous solution was diluted to 150 mL with water
  3. additionacidified to pH 2 by addition of 6 M HCl
  4. stirringwhile stirring vigorously
  5. filtrationThe precipitate was collected by filtration
  6. washrinsed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c970950bfc924c178eb4720cec3984f4
Source dataset
uspto-grants-2014_07
Patent number
US08778950B2

Reaction notes

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