Tris(hydroxymethyl)aminomethane → HCID 11428128, compound

HRID 1952867Notes

Reaction equation

HRID 1952867 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([NH:10][C:11]2[S:12][C:13]([CH:16]([CH3:18])[CH3:17])=[CH:14][N:15]=2)=[O:9])[N:6]=1.[CH2:19](O)[C:20](N)([CH2:23]O)[CH2:21][OH:22].C(OC(C)C)(C)C>C(Cl)Cl.C1(N=C=N)CCCCC1.C(Cl)Cl.CN(C=O)C>[CH:16]([C:13]1[S:12][C:11]([NH:10][C:8](=[O:9])[CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:21](=[O:22])[CH:20]([CH3:23])[CH3:19])[S:3][CH:4]=2)=[N:15][CH:14]=1)([CH3:18])[CH3:17]

Participants

7

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 7914Diisopropyl EtherHCID 11323531HCID 11323531, compound

Product 1

HCID 11428128HCID 11428128, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 12048208N-CyclohexylcarbodiimideSolventHCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of isobutyrric acid (49 μl, 0.53 mmol) in CH2Cl2 (1.5 ml), N-cyclohexylcarbodiimide, N'-methyl polystyrene (0.4 g, loading 2 mmol/g, 0.798 mmol), Nhydroxybenzotriazole (0.072 g, 0.53 mmol) and a solution of 2-(2-amino-1,3-thiazol-4-yl)-N-(5-isopropyl-1,3-thiazol-2-yl)acetamide (0.075 g, 0.266 mmol) in CH2Cl2 /DMF (0.4 ml/0.6 ml) were added. The reaction mixture was maintained under stirring at room temperature for about 8 days. After this time, PS-Trisamine (0.44 g, loading 3.62 mmol/g, 1.596 mmol) was added, stirring was continued for about 6 hours and then the mixture was filtered. The resin was washed with CH2Cl2 (1 ml×5), the organic layers were combined and evaporated to dryness to give, after trituration with diisopropyl ether the title compound.

Workup

  1. temperatureThe reaction mixture was maintained
  2. stirringstirring
  3. waitwas continued for about 6 hours
  4. filtrationthe mixture was filtered
  5. washThe resin was washed with CH2Cl2 (1 ml×5)
  6. customevaporated to dryness
  7. customto give

Sources & evidence

ORD record
ord-9b7131b03ab04a2f9535772303f209a6
Source dataset
uspto-grants-2000_09
Patent number
US06114365

Reaction notes

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