Tetrahydrofuran → HCID 68679919, compound

HRID 1444735Notes

Reaction equation

HRID 1444735 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]([N:22]2[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24][CH2:23]2)=[O:21])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:30]1COCC1.C[Mg]Br.O.O.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]2[CH:17]=[CH:16][NH:15][C:14](=[O:18])[C@H:13]2[CH2:19][C:20]([N:22]2[CH2:28][CH2:27][CH2:26][C:25]([OH:29])([CH3:30])[CH2:24][CH2:23]2)=[O:21])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11547106HCID 11547106, compoundHCID 86602832HCID 86602832, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 68679919HCID 68679919, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-1-(2-(1-(3,4-dichlorophenylsulfonyl)-3-oxo-1,2,3,4-tetrahydropyrazin-2-yl)acetyl)azepan-4-one (4) (0.0250 g, 0.054 mmol) in THF (8.00 ml, 0.054 mmol) under N2 was added methylmagnesium bromide (1.4M solution in THF/Toluene (75:25), 2.70 ml, 3.78 mmol) in thee times, and stirred overnight. The reaction mixture was cooled in ice-water bath and sodium sulfate dodecahydrate (10.0 g) was added slowly followed by AcOEt (20 ml). After stirring at r.t. for 1 h, the mixture was filtered and the solid was washed with AcOEt. The filtrate was concentrated under reduced pressure and the crude product was chomatographed on silica (CH2Cl2→CH2Cl2/MeOH=20/1) to yield the product. MS 476 (M+H).

Workup

  1. stirringAfter stirring at r.t. for 1 h
  2. filtrationthe mixture was filtered
  3. washthe solid was washed with AcOEt
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto yield the product

Sources & evidence

ORD record
ord-5af5cbf265294be385099210fb690901
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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