1,1'-Carbonyldiimidazole → 2-trityl-2H-tetrazol-5-yl-acetamide

HRID 643263Notes

Reaction equation

HRID 643263 reaction equation
[C:1]([N:20]1[N:24]=[N:23][C:22]([CH2:25][C:26]([OH:28])=O)=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=C[N:31](C(N2C=NC=C2)=O)C=1.NC1C=CC(C(N2CC3(C)CC2CC(C)(C)C3)=O)=CC=1>C1COCC1>[C:1]([N:20]1[N:24]=[N:23][C:22]([CH2:25][C:26]([NH2:31])=[O:28])=[N:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 577868(4-Amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanoneHCID 22405503(2-trityl-2H-tetrazol-5-yl)-acetic acid

Product 1

HCID 1317280592-trityl-2H-tetrazol-5-yl-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-trityl-2H-tetrazol-5-yl)-acetic acid (0.82 g, 2.20 mmol) in dry THF (50 ml) was added CDI (0.4 g, 2.39 mmol) and the resulting mixture was stirred for 10 min. To this mixture was added (4-amino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (0.5 g, 1.84 mmol) and the stirring was continued for 18 hrs. at room temperature. The mixture was evaporated and the residue purified by column chromatography (silica gel) using EtOAc-Heptane (4:1) as eluent. Pure fractions were collected and evaporated to dryness affording 150 mg (13%) of N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-2-(2-trityl-2H-tetrazol-5-yl-acetamide which was dissolved in THF (25 ml) followed by addition of 20% aqueous HCl (20 ml). The mixture was stirred for 2 hrs. at room temperature at which time the volatiles were removed in vacuo. The aqueous residue was extracted with EtOAc (2×50 ml), dried (Na2SO4), filtered and evaporated in vacuo affording 30 mg (4%) of the title compound as a solid.

Workup

  1. waitthe stirring was continued for 18 hrs
  2. customat room temperature
  3. customThe mixture was evaporated
  4. customthe residue purified by column chromatography (silica gel)
  5. customPure fractions were collected
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-03791ba44af04fc891d2e2255101534c
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

Loading…