Dichloromethane → HCID 86628209, compound

HRID 1821367Notes

Reaction equation

HRID 1821367 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2/[CH:18]=[CH:19]/[C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][N:21]=2)[S:9][CH:10]=1)=O)C.C(Cl)Cl.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[NH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20](/[CH:19]=[CH:18]/[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:8]2[S:9][CH:10]=[C:6]([CH2:4][OH:3])[N:7]=2)=[N:21]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 86628207HCID 86628207, compound

Product 1

HCID 86628209HCID 86628209, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 169 (0.04 g, 0.10 mmol) was dissolved in THF (1.0 mL) and methylene chloride (1.0 mL) and after cooling to −78° C., diisobutylaluminum hydride (0.95 mol/L toluene solution, 0.65 mL, 0.62 mmol) was added and stirred in a temperature between −78° C. to room temperature for 19 hours. Saturated aqueous Rochelle salt solution was added to the mixture and the organic layer was extracted with ethyl acetate. The organic layer was concentrated and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1). Then, the mixture was triturated in ethanol to obtain Compound 173 (16 mg, 44%).

Workup

  1. extractionthe organic layer was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)
  4. customThen, the mixture was triturated in ethanol

Sources & evidence

ORD record
ord-f95ab89c9b414aac837d0e5d9ae29b37
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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