Water → HCID 86714052, compound

HRID 576343Notes

Reaction equation

HRID 576343 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C@H:10]2[C@H:15]([OH:16])[C@@H:14]([OH:17])[C@H:13]([OH:18])[C@@H:12]([CH2:19][OH:20])[O:11]2)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=1.[H-].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O>CN(C=O)C.C1COCC1>[CH2:33]([O:18][C@H:13]1[C@H:14]([O:17][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:15]([O:16][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:10]([C:5]2[CH:6]=[C:7]([O:8][CH3:9])[C:2]([Cl:1])=[C:3]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=3)[CH:4]=2)[O:11][C@@H:12]1[CH2:19][O:20][CH2:10][C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 71076877HCID 71076877, compound

Product 1

HCID 86714052HCID 86714052, compoundYield 182.2%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of compound 75 (4.12 mmol) in DMF/THF (20 mL/60 mL) at 0° C. under an atmosphere of nitrogen were added NaH (60% oil, 825 mg, 20.6 mmol) and benzyl bromide (4.9 mL, 41.2 mmol) dropwise, and the mixture was stirred for 16 hours at the room temperature. To the mixture was added water (20 mL) to quench the reaction. After dilution with water, the mixture was stirred at room temperature for 30 min and extracted with EtOAc (200 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 76 (3.0 g, 93%) as colorless oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionextracted with EtOAc (200 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c9ce1b99d5c1450ba54ff128a2a6df54
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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