Triethylamine → HCID 117702317, compound

HRID 629920Notes

Reaction equation

HRID 629920 reaction equation
[CH3:1][C:2]([CH3:21])([CH3:20])[CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([C@H:13]([CH2:15][CH2:16]O)[CH3:14])=[CH:10][CH:11]=2)[N:6]([CH3:18])[C:5]1=[O:19].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>ClCCl>[N:34]([CH2:16][CH2:15][C@@H:13]([C:9]1[N:8]=[C:7]2[N:6]([CH3:18])[C:5](=[O:19])[N:4]([CH2:3][C:2]([CH3:21])([CH3:20])[CH3:1])[C:12]2=[CH:11][CH:10]=1)[CH3:14])=[N+:35]=[N-:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 117702580HCID 117702580, compound

Product 1

HCID 117702317HCID 117702317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 36-2 (0.15 g, 0.52 mmol) in dichloromethane (2 mL) was added triethylamine (0.15 mL, 1.08 mmol) and methanesulfonyl chloride (0.05 mL, 0.62 mmol). The resulting mixture was stirred at room temperature for 10 minutes and concentrated. The residue was dissolved in DMF (2 mL). To this solution was added sodium azide (0.20 g, 3.08 mmol) and the mixture was heated to 90° C. for 3 days. The reaction was allowed to cool and partitioned between ethyl acetate and water. The organic phase was concentrated to give 36-3. (0.13 g, 83%). LRMS (ES) (M+H)+: observed=317.1, calculated=317.4.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DMF (2 mL)
  3. temperaturethe mixture was heated to 90° C. for 3 days
  4. temperatureto cool
  5. custompartitioned between ethyl acetate and water
  6. concentrationThe organic phase was concentrated
  7. customto give 36-3

Sources & evidence

ORD record
ord-37ca57f5c8b242f2bf099e8dcaab12a6
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

Loading…