Ethyl bromoacetate → HCID 19081174, compound

HRID 963525Notes

Reaction equation

HRID 963525 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]([OH:41])[CH:36]=3)=[O:33])[C:14]1=[O:42])=[O:11])[CH2:2]2.C(=O)([O-])[O-].Br[CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50].C(OCC)(=O)C>CN(C)C=O.O>[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]([O:41][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[CH:36]=3)=[O:33])[C:14]1=[O:42])=[O:11])[CH2:4]2

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 19081228HCID 19081228, compound

Product 1

HCID 19081174HCID 19081174, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[(3RS)-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-hydroxyphenyl)urea, pottasium carbonate and ethyl bromoacetate in dimethylformamide was stirred at room temperature for 4 hours. Ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. The organic solvent was evaporated to dryness, and washed with isopropyl ether and vacuumed to afford N-[(3RS)-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-(ethoxycarbonylmethoxy)phenyl]urea.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe organic solvent was evaporated to dryness
  5. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-de38007a22fa457089fbdd3f5f5b3572
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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