Sodium Hydroxide → HCID 19081179, compound

HRID 963527Notes

Reaction equation

HRID 963527 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:16][CH:15]([NH:31][C:32]([NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([O:43]C)=[O:42])[CH:36]=3)=[O:33])[C:14]1=[O:45])=[O:11])[CH2:2]2.[OH-].[Na+]>O1CCCC1>[CH:5]12[CH2:6][CH2:7][CH:1]([CH2:9][CH2:8]1)[CH2:2][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[F:30])=[N:16][CH:15]([NH:31][C:32]([NH:34][C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([OH:43])=[O:42])[CH:36]=3)=[O:33])[C:14]1=[O:45])=[O:11])[CH2:4]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19081287HCID 19081287, compound

Product 1

HCID 19081179HCID 19081179, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-[1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methoxycarbonylphenyl)urea (312.5 mg) and 0.1N sodium hydroxide (7.7 ml, 1.5 eq. mol) in tetrahydrofuran (20 ml) was refluxed under stirring for 7 hours. After removal of the tetrahydrofuran, the residual aqueous mixture was extracted with ethyl acetate. After the separated aqueous layer was washed with ethyl acetate, it was acidified with diluted hydrochloric acid. The resultant precipitates were collected by filtration, washed with water and dried under reduced pressure to afford N-[1-(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl-2,3-dihydro-5-(2-fluorophenyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-carboxyphenyl)urea (0.19 g, 62.2%) as a white crystalline powder.

Workup

  1. temperaturewas refluxed
  2. customAfter removal of the tetrahydrofuran
  3. extractionthe residual aqueous mixture was extracted with ethyl acetate
  4. washAfter the separated aqueous layer was washed with ethyl acetate, it
  5. customThe resultant precipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-759e0d7a8d8b4d1ba16082158ace464a
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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