HCID 23574474, compound → HCID 22046633, compound

HRID 1826144Notes

Reaction equation

HRID 1826144 reaction equation
[CH2:1]([O:8][C:9]1[C:32]([O:33][CH3:34])=[CH:31][C:12]2[C:13](=[O:30])[N:14]3[CH2:29][CH2:28][CH2:27][C@H:15]3[C@H:16](O)[N:17](C(OCC(Cl)(Cl)Cl)=O)[C:11]=2[C:10]=1[O:35][CH3:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.CCOC(C)=O>[CH2:1]([O:8][C:9]1[C:32]([O:33][CH3:34])=[CH:31][C:12]2[C:13](=[O:30])[N:14]3[CH2:29][CH2:28][CH2:27][CH:15]3[CH:16]=[N:17][C:11]=2[C:10]=1[O:35][CH3:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23574474HCID 23574474, compound

Product 1

HCID 22046633HCID 22046633, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

10% Cd/Pb couple (1.2 g; 10 mmol Cd) was added to a rapidly stirring solution of 142 (1.08 g; 1.9 mmol) in a mixture of THF (15 mL) and 1N NH4OAc (15 mL). After 3.5 h, TLC revealed that reaction was still incomplete and more 10% Cd/Pb couple (500 mg) was added. After a further 1 hour the reaction mixture was diluted with EtOAc (150 mL). The solution was dried over anhydrous MgSO4 and the solids were filtered and rinsed with EtOAc (50 mL). Removal of excess solvent yielded the product as a yellow glass (0.48 g, 1.3 mmol, 68%). H1NMR (270 MHz, CDCl3) δ 7.73 (d, 1H, J=4.4 Hz), 7.36 (s, 2H), 7.31 (s, 2H), 7.11 (s, 1H), 7.08 (s, 1H), 5.12 (br s, 2H), 3.98-3.42 (m, 9H), 2.38-2.29 (m, 2H), 2.23-1.83 (m, 2H).

Workup

  1. customTLC revealed that reaction
  2. dry with materialThe solution was dried over anhydrous MgSO4
  3. filtrationthe solids were filtered
  4. washrinsed with EtOAc (50 mL)
  5. customRemoval of excess solvent

Sources & evidence

ORD record
ord-6d89839fe0cb4bccb0a4ef8df90e75d8
Source dataset
uspto-grants-2006_05
Patent number
US07049311B1

Reaction notes

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