Ammonium Bicarbonate → HCID 58743884, compound

HRID 1437316Notes

Reaction equation

HRID 1437316 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH2:18][C:13]([C:19]([OH:21])=O)([CH:14]=[CH:15]2)[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:23]1C2N=CC=CC=2N=N1.C(=O)([O-])O.[NH4+]>CN(C=O)C.O>[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH2:18][C:13]([C:19](=[O:21])[NH2:23])([CH:14]=[CH:15]2)[O:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14013Ammonium Bicarbonate2×HCID 181649HOAtHCID 58743880HCID 58743880, compound

Product 1

HCID 58743884HCID 58743884, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The benzyl ester (d) (12.0 g, 41.5 mmol) and 1-hydroxy-7-azabenzotriazole (6.26 g, 46 mmol) were dissolved in DMF (100 ml) then I-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (8.79 g, 46 mmol) added. After stirring for 5 minutes ammonium hydrogen carbonate (8.22 g, 104 mmol) was added. Four further small portions of ammonium hydrogen carbonate were added over the next 7 hours. The mixture was then stirred overnight, diluted with water and extracted with ethyl acetate (×4). The combined organic extracts were washed with 5% aqueous citric acid then brine, dried and evaporated to give an off-white solid (9.9 g, 83%).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (×4)
  3. washThe combined organic extracts were washed with 5% aqueous citric acid
  4. dry with materialbrine, dried
  5. customevaporated

Sources & evidence

ORD record
ord-2be4c219507447a080a1398af89fb402
Source dataset
uspto-grants-2009_11
Patent number
US07622481B2

Reaction notes

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