HCID 90829811, compound → HCID 91474047, compound

HRID 1357507Notes

Reaction equation

HRID 1357507 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[C:5]([NH:8][C@@H:9]1[C:14](=[O:15])[CH2:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C@H:10]1[O:20][CH:21]([CH3:23])[CH3:22])(=[O:7])[CH3:6]>C1COCC1>[C:5]([NH:8][C@@H:9]1[C@@:14]([OH:15])([CH:1]=[CH2:2])[CH2:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C@H:10]1[O:20][CH:21]([CH3:23])[CH3:22])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 90829811HCID 90829811, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 91474047HCID 91474047, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Vinylmagnesium bromide can be added to a −78° C. solution of Example 16A in THF. The reaction mixture can be stirred for 2 hours and quenched with saturated aqueous NH4Cl. The quenched reaction mixture can be extracted several times with dichloromethane. The combined dichloromethane layers can be dried (MgSO4), filtered and concentrated. The concentrate can be purified by column chromatography to afford the desired product.

Workup

  1. customquenched with saturated aqueous NH4Cl
  2. customThe quenched reaction mixture
  3. extractioncan be extracted several times with dichloromethane
  4. dry with materialThe combined dichloromethane layers can be dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe concentrate can
  8. custombe purified by column chromatography

Sources & evidence

ORD record
ord-3ac459ff397647b892e44ec9d35eed6c
Source dataset
uspto-grants-2003_07
Patent number
US06593314B1

Reaction notes

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