Carbonate Ion → HCID 58503944, compound

HRID 2407739Notes

Reaction equation

HRID 2407739 reaction equation
[C:1]([CH:3]([C:19]1[S:23][C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[N:21][CH:20]=1)[N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11]C(=O)OC(C)(C)C)[CH2:6][CH2:5]1)#[N:2].C([NH+](CC)CC)C.C(=O)([O-])[O-]>ClCCl.FC(F)(F)C(O)=O>[NH2:11][CH2:10][CH:7]1[CH2:6][CH2:5][N:4]([CH:3]([C:19]2[S:23][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:21][CH:20]=2)[C:1]#[N:2])[CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 19660Carbonate IonHCID 1385867TriethylammoniumHCID 58503942HCID 58503942, compound

Product 1

HCID 58503944HCID 58503944, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The compound prepared in Example 235 (0.14 g) was dissolved in dichloromethane (2 mL) and trifluoroacetic acid (0.4 mL). The reaction was stirred for 1 hour and then concentrated and pumped to dryness. The amine salt was dissolved in tetrahydrofuran (5 mL) and Macroporous triethylammonium methylpolystyrene carbonate (MP-carbonate: Argonaut Technologies catalog number 80,026-9; 0.65 g) (2.5-3.5 mmol/g) 1.6-2.2 mmol was added. After 2 hours of stirring the reaction was filtered, washed with tetrahydrofuran, concentrated and used without further purification.

Workup

  1. concentrationconcentrated
  2. dissolutionThe amine salt was dissolved in tetrahydrofuran (5 mL)
  3. stirringAfter 2 hours of stirring the reaction
  4. filtrationwas filtered
  5. washwashed with tetrahydrofuran
  6. concentrationconcentrated
  7. customused without further purification

Sources & evidence

ORD record
ord-f0391bbb67eb480084157a2e1ce128cd
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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