Ammonium Bicarbonate → HCID 68697939, compound

HRID 1437384Notes

Reaction equation

HRID 1437384 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15](O)=[O:16])[CH2:11][C@H:10]1[O:18][CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:21]1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(=O)([O-])O.[NH4+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]1[CH2:14][CH2:13][C@@H:12]([C:15](=[O:16])[NH2:21])[CH2:11][C@H:10]1[O:18][CH3:19])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 14013Ammonium BicarbonateHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68700284HCID 68700284, compound

Product 1

HCID 68697939HCID 68697939, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the acid (f) (5.0 g, 18 mmol) and 1-hydroxy-7-azabenzotriazole (2.73 g, 20 mmol) in DMF (200 ml) was treated with (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (3.87 g, 20 mmol) and ammonium hydrogen carbonate (5.8 g, 73 mmol). The mixture was stirred at room temperature for 18 hours then evaporated to dryness. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The organic extract was dried and evaporated. Trituration with ether and filtration afforded a white solid (3.72 g, 75%).

Workup

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. extractionThe organic extract
  4. customwas dried
  5. customevaporated
  6. filtrationTrituration with ether and filtration

Sources & evidence

ORD record
ord-992b3701e03f4cb9894b71198317554a
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

Loading…