Triethylamine → HCID 72338940, compound

HRID 1873551Notes

Reaction equation

HRID 1873551 reaction equation
[CH2:1]([C:3]1([C:16]([OH:18])=O)[CH2:15][CH:6]2[CH2:7][N:8]([C:10](=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:9][CH:5]2[CH2:4]1)[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[N-:32]=[N+:33]=[N-:34].[Na+]>CC(C)=O.O>[CH2:1]([C:3]1([C:16]([N:32]=[N+:33]=[N-:34])=[O:18])[CH2:15][CH:6]2[CH2:7][N:8]([C:10](=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:9][CH:5]2[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 68625771HCID 68625771, compound

Product 1

HCID 72338940HCID 72338940, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

5-Ethyl-2-dimethylcarbamoyl-hexahydro-cyclopenta[c]pyrrole-5-carboxylic acid 19c (0.56 g, 2.2 mmol) was dissolved in 60 mL of acetone upon cooling by an ice-water bath. When cooled to −5° C., triethylamine (0.245 mg, 2.43 mmol) and a solution of 2 mL of ethyl chloroformate (263 mg, 2.43 mmol) in acetone were added dropwise. After the reaction mixture was stirred for 15 minutes, a solution of sodium azide (0.286 g, 4.4 mmol) in 2 mL of water was added. The reaction mixture was stirred at −5° C.˜0° C. for another 30 minutes. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 10 mL of water, extracted with ethyl acetate (10 mL×5). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-ethyl-2-dimethylcarbamoyl-hexahydro-cyclopenta[c]pyrrole-5-carbonyl azide 19d (0.5 g) as a light yellow oil which was directly used in the next step.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. stirringThe reaction mixture was stirred at −5° C.˜0° C. for another 30 minutes
  3. extractionextracted with ethyl acetate (10 mL×5)
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f91a6cec802f465d95cfd4facd53477b
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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