Triethylamine → HCID 86695274, compound

HRID 709409Notes

Reaction equation

HRID 709409 reaction equation
ClC(OCC)=O.[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[CH2:23][C@H:22]2[C:24]([OH:26])=O)=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[N-:34]=[N+:35]=[N-:36].[Na+]>CC(C)=O.O>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]2[CH2:23][C@H:22]2[C:24]([N:34]=[N+:35]=[N-:36])=[O:26])=[CH:17][CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 518881081257122-75-02×

Product 1

HCID 86695274HCID 86695274, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Ethyl chloroformate (143 mL, 1.48 mol) was added to a solution of (trans)-2-(4-(benzyloxy) phenyl)cyclopropanecarboxylic acid (Intermediate S, 190 g, 0.70 mol), Triethyl amine (229 mL, 1.63 mol) in acetone (2.8 L) at −20° C. and stirred for 1 h, then a solution of NaN3 (138 g, 2.1 mol) in water (200 mL) was added and stirred at RT for 30 mins. After completion, the solvent was evaporated, residue was dissolved in EtOAc (2 L), washed with water (2 L), brine (1 L), dried over anhydrous Na2SO4, filtered and evaporated to afford (trans)-2-(4-(benzyloxy)phenyl)cyclopropanecarbonyl azide (178 g, 85.9%).

Workup

  1. stirringstirred at RT for 30 mins
  2. customAfter completion, the solvent was evaporated
  3. dissolutionresidue was dissolved in EtOAc (2 L)
  4. washwashed with water (2 L), brine (1 L)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-71e0b42002b840a4b89f3e461c7341c3
Source dataset
uspto-grants-2015_11
Patent number
US09181198B2

Reaction notes

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