Triethylamine → HCID 72338924, compound

HRID 1961605Notes

Reaction equation

HRID 1961605 reaction equation
[CH:1]1([C:6]2([C:19]([OH:21])=O)[CH2:18][CH:9]3[CH2:10][N:11]([C:13](=[O:17])[N:14]([CH3:16])[CH3:15])[CH2:12][CH:8]3[CH2:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(OCC)=O.[N-:35]=[N+:36]=[N-:37].[Na+]>CC(C)=O.O>[CH:1]1([C:6]2([C:19]([N:35]=[N+:36]=[N-:37])=[O:21])[CH2:18][CH:9]3[CH2:10][N:11]([C:13](=[O:17])[N:14]([CH3:15])[CH3:16])[CH2:12][CH:8]3[CH2:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 68626053HCID 68626053, compound

Product 1

HCID 72338924HCID 72338924, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

5-Cyclopentyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 16c (0.28 g, 6.95 mmol) was dissolved in 20 mL of acetone upon cooling by an ice-water bath, followed by addition of triethylamine (0.15 mL, 1.05 mmol) and a solution of 2 mL of ethyl chloroformate (0.1 mL, 1.05 mmol) in acetone at 0° C.˜−5° C. After the reaction mixture was stirred for 15 minutes, a solution of sodium azide (0.124 g, 1.9 mmol) in water was added dropwise. 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 and the residue was diluted with 10 mL of water. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-cyclopentyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carbonyl azide 16d (0.287 g, yield 95%) as a yellow oil which was directly used in the next step.

Workup

  1. temperatureupon cooling by an ice-water bath
  2. customat 0° C.˜−5° C
  3. stirringThe reaction mixture was stirred for another 30 minutes
  4. concentrationThe mixture was concentrated
  5. additionthe residue was diluted with 10 mL of water
  6. extractionThe mixture was extracted with ethyl acetate
  7. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c42227f0439f424eba61fa4077ccfa65
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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