1,1'-Carbonyldiimidazole → HCID 66742386, compound

HRID 1960195Notes

Reaction equation

HRID 1960195 reaction equation
S(C1C=CC(C)=CC=1)(O)(=O)=O.[NH2:12][C@:13]1([C:18]([O:20][CH3:21])=[O:19])[CH2:15][C@H:14]1[CH:16]=[CH2:17].[CH:22]1[N:26]=[CH:25][N:24]([C:27](N2C=NC=C2)=[O:28])[CH:23]=1>C1COCC1>[N:24]1([C:27]([NH:12][C@:13]2([C:18]([O:20][CH3:21])=[O:19])[CH2:15][C@H:14]2[CH:16]=[CH2:17])=[O:28])[CH:23]=[CH:22][N:26]=[CH:25]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 114498134-Methylbenzene-1-sulfonic acid--methyl 1-amino-2-ethenylcyclopropane-1-carboxylate (1/1)

Product 1

HCID 66742386HCID 66742386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound BT was prepared according to Scheme 12. To a suspension of (1R,2S)-methyl 1-amino-2-vinylcyclopropanecarboxylate tosylate salt (25.0 g, 1 eq.) in THF (150 mL) at 50° C. were added CDI (14.24 g, 1.1 eq.) and TEA (12.27 mL, 1.1 eq.). The reaction mixture was then refluxed overnight. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc, and washed with water. The organic layer was dried over sodium sulfate and concentrated. The residue was triturated in Et2O to afford compound BT (15.24 g, purity 80%) as a white solid. 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.63 (dd, J=5.8 and 9.7 Hz, 1H), 1.96 (dd, J=5.8 and 8.4 Hz, 1H), 2.30 (q, J=8.9 Hz, 1H), 3.73 (s, 3H), 5.16 (d, J=10.0 Hz, 1H), 5.28 (d, J=17.0 Hz, 1H), 5.69-5.81 (m, 1H), 7.03 (s, 1H), 7.50 (s, 1H), 8.24 (s, 1H), 8.57 (s, 1H).

Workup

  1. customCompound BT was prepared
  2. temperatureThe reaction mixture was then refluxed overnight
  3. customThe solvent was removed under reduced pressure
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with water
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was triturated in Et2O
  9. customto afford compound BT (15.24 g, purity 80%) as a white solid

Sources & evidence

ORD record
ord-e3cf945a95b54701b54cbddbff4f1a1a
Source dataset
uspto-grants-2013_04
Patent number
US08410313B2

Reaction notes

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