Sodium Hydroxide → HCID 178518239, compound

HRID 1596164Notes

Reaction equation

HRID 1596164 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([C:10]3[C:15](=[O:16])[NH:14][C:12](=[O:13])[C:11]=3[C:17]3[NH:21][CH:20]=[N:19][CH:18]=3)=[CH:8][NH:9][C:4]2=[CH:3][CH:2]=1.[OH-].[Na+]>CC(=O)CC.CCOC(C)=O>[CH:1]1[CH:2]=[CH:3][C:4]2[NH:9][C:8]3[N:21]4[C:17](=[CH:18][N:19]=[CH:20]4)[C:11]4[C:12]([NH:14][C:15](=[O:16])[C:10]=4[C:7]=3[C:5]=2[CH:6]=1)=[O:13]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 398493HCID 398493, compound

Product 1

HCID 178518239HCID 178518239, compoundYield 38.1%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of didemnimide A (32.6 mg, 0.117 mmol) in 2-butanone (7.0 mL) at rt is added sequentially 4Å molecular sieves (˜100 mg) and CUCl2 (79 mg, 0.59 mmol). The reaction mixture was stirred for 15 h at rt. The dark purple solution was treated with 10% solution of NaOH until the pH was neutral and diluted with EtOAc (30 mL). The phases were separated and the aqueous layer was extracted with EtOAc (5×10 mL). The combined organic extracts were washed with brine (10 mL), dried (MgSO4) and concentrated. Flash chromatography (15 g of silica gel, 15:1 CH2Cl2—MeOH) of the crude material afforded 19.5 mg (60%) of recovered didemnamide A as well as 12.3 mg (38%, 95% based on recovered starting material) of iso-granulatimide (5) as a purple solid.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with EtOAc (5×10 mL)
  3. washThe combined organic extracts were washed with brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c6107b9b669485a8a6ce4066d7ecfe9
Source dataset
uspto-grants-2001_09
Patent number
US06291447B1

Reaction notes

Loading…