Ammonia → HCID 15289131, compound

HRID 1290863Notes

Reaction equation

HRID 1290863 reaction equation
C([N:3](CC)CC)C.ClC(OC)=O.[CH2:13]([N:20]1[C:28](=[O:29])[CH:27]2[CH:22]([C:23]3([C:31](O)=[O:32])[CH2:30][CH:26]2[CH:25]=[CH:24]3)[C:21]1=[O:34])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N>O1CCCC1>[CH2:13]([N:20]1[C:28](=[O:29])[CH:27]2[CH:22]([C:23]3([C:31]([NH2:3])=[O:32])[CH2:30][CH:26]2[CH:25]=[CH:24]3)[C:21]1=[O:34])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 15289130HCID 15289130, compound

Product 1

HCID 15289131HCID 15289131, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.1 g (11 mmol) of triethylamine and then 1.15 g (12 mmol) of methyl chloroformate are added dropwise to 3 g (10 mmol) of 4-benzyl-3,5-dioxo-4-azatricyclo[5.2.1.02,6 ]dec-8-ene-1-carboxylic acid in 20 ml of absolute tetrahydrofuran at 0° C. The mixture is stirred at 0° C. for a further hour and the solution is poured onto 20 ml of ammonia solution. The mixture is stirred at room temperature for 1 hour and extracted several times with chloroform, and the extracts are dried over MgSO4 and concentrated, whereupon the product crystallizes.

Workup

  1. stirringThe mixture is stirred at room temperature for 1 hour
  2. extractionextracted several times with chloroform
  3. dry with materialthe extracts are dried over MgSO4
  4. concentrationconcentrated, whereupon the product
  5. customcrystallizes

Sources & evidence

ORD record
ord-49255764077b4bb09955a919595d7bf0
Source dataset
uspto-grants-1998_05
Patent number
US05753669

Reaction notes

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