Triethylamine → HCID 72338930, compound

HRID 1873532Notes

Reaction equation

HRID 1873532 reaction equation
[CH2:1]([C:8]1([C:21]([OH:23])=O)[CH2:20][CH:11]2[CH2:12][N:13]([C:15](=[O:19])[N:16]([CH3:18])[CH3:17])[CH2:14][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O.[N-:37]=[N+:38]=[N-:39].[Na+]>CC(C)=O.O>[CH2:1]([C:8]1([C:21]([N:37]=[N+:38]=[N-:39])=[O:23])[CH2:9][CH:10]2[CH2:14][N:13]([C:15](=[O:19])[N:16]([CH3:17])[CH3:18])[CH2:12][CH:11]2[CH2:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 68625833HCID 68625833, compound

Product 1

HCID 72338930HCID 72338930, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-5 °C

Procedure

5-Benzyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 14c (0.86 g, 2.72 mmol) was dissolved in 30 mL of acetone upon cooling by an ice-water bath. When the mixture was cooled to −5° C., a solution of triethylamine (0.303 g, 2.99 mmol) and ethyl chloroformate (0.325 g, 2.99 mmol) in 15 mL of acetone were added dropwise successively. The reaction mixture was stirred for 15 minutes followed by dropwise addition of a solution of sodium azide (0.353 g, 5.44 mmol) in 15 mL of water. The reaction mixture was stirred for another 30 minutes. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated under reduced pressure and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-benzyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carbonyl azide 14d (0.9 g, yield 97%) as a light yellow oil.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. stirringThe reaction mixture was stirred for another 30 minutes
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-290bb6d19b434c08b85717378e99e220
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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