Water → HCID 52951165, compound

HRID 508600Notes

Reaction equation

HRID 508600 reaction equation
[C:1]1([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18](=[O:21])(=[O:20])[NH2:19])=[CH:14][CH:13]=3)[N:10]=[C:9](C(O)=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:27](CC)CC.[CH3:32][CH2:33][O:34][C:35](C)=[O:36].O>CCO.O1CCOCC1>[CH2:33]([O:34][C:35](=[O:36])[NH:27][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:11]([C:12]2[CH:13]=[CH:14][C:15]([S:18](=[O:20])(=[O:21])[NH2:19])=[CH:16][CH:17]=2)[N:10]=1)[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10043064HCID 10043064, compound

Product 1

HCID 52951165HCID 52951165, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of acid 4 (0.74 g, 2 mmol) in 10 mL of EtOH and 10 mL of 1,4-dioxane was added diphenylphosphonylazide (0.52 mL, 2.4 mmol) followed by Et3N (0.34 mL, 2.4 mmol). The reaction mixture was refluxed overnight. After cooling the reaction mixture to room temperature, EtOAc and water were added. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography to give the titled compound (0.48 g, 62%) as a white solid. mp 120.9-127.5° C. 1H NMR (300 MHz, DMSO-d6): δ 10.30 (s, 1H), 7.79 (d, J=8 Hz, 2H), 7.50-7.34 (m, 7H), 7.33-7.25 (m, 2H), 6.74 (s, 1H), 4.14 (q, J=7 Hz, 2H), 1.24 (t, J=7 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-bec77657c8f5422fac0ddafbccccf586
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

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