Toluene → HCID 58947963, compound

HRID 1160148Notes

Reaction equation

HRID 1160148 reaction equation
C1(C)C=CC=CC=1.[CH:8]1([N:11]([CH3:25])[S:12]([CH2:15][C:16]2(C(O)=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:14])=[O:13])[CH2:10][CH2:9]1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])=CC=1.CC[N:45]([CH2:48]C)CC>C(Cl)Cl>[CH:8]1([N:11]([CH3:25])[S:12]([CH2:15][C:16]2([N:45]=[C:48]=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)(=[O:13])=[O:14])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58947949HCID 58947949, compound

Product 1

HCID 58947963HCID 58947963, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a RT solution of toluene (15 mL) containing acid 1261-F (3.96 mmol, 1.0 g) was added DPPA (0.85 mL, 3.96 mmol) followed by Et3N (0.56 mL, 3.96 mmol). The reaction was stirred at RT for 10 min then refluxed for 2 hours. Reaction was cooled down to RT and diluted with DCM (50 mL). Washed with NaHCO3, brine and organic layer was dried over MgSO4. The volatile were removed and the residue was diluted with DCM (15 mL) to give 1261-G as a 0.26M solution.

Workup

  1. temperaturethen refluxed for 2 hours
  2. customReaction
  3. temperaturewas cooled down to RT
  4. washWashed with NaHCO3, brine and organic layer
  5. dry with materialwas dried over MgSO4
  6. customThe volatile were removed
  7. additionthe residue was diluted with DCM (15 mL)

Sources & evidence

ORD record
ord-a2ac4ee5652d44e98b3ccf91e067e0c5
Source dataset
uspto-grants-2010_10
Patent number
US07816326B2

Reaction notes

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