Potassium Carbonate → HCID 66813395, compound

HRID 504255Notes

Reaction equation

HRID 504255 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:19]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1.[NH2:39][CH2:40][CH2:41][NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:46]([O:45][C:43](=[O:44])[NH:42][CH2:41][CH2:40][NH:39][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:19]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:18]=[N:17][N:16]=2)=[CH:5][CH:4]=1)([CH3:49])([CH3:47])[CH3:48]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 187201N-BOC-ethylenediamineHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Product 1

HCID 66813395HCID 66813395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(4′-bromomethylbiphenyl-2-yl)-1-trityl-1H-tetrazole made as described in Preparation 1 (20.9 g, 37.4 mmol), N-(2-aminoethyl)(t-butoxy) carboxamide (15 g, 93.6 mmol), and potassium carbonate (10.4 g, 74.9 mmol) in THF (150 mL) was stirred overnight at room temperature. The solvent was removed in vacuo and extracted with 1M aqueous KOH (70 mL) and DCM (3×200 mL). The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. The crude intermediate (2a) was used in the next step.

Workup

  1. customThe solvent was removed in vacuo
  2. extractionextracted with 1M aqueous KOH (70 mL) and DCM (3×200 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7eac18e8403d4c0eaa7763884e9dc308
Source dataset
uspto-grants-2010_08
Patent number
US07777077B2

Reaction notes

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