HCID 86584855, compound → HCID 69428524, compound

HRID 458363Notes

Reaction equation

HRID 458363 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH2:23][CH2:24][C:25](=[O:30])N(OC)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:31][C:32]1[CH:37]=[CH:36][C:35]([Mg]Br)=[CH:34][CH:33]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH2:10][C@H:9]1[CH2:23][CH2:24][C:25]([C:35]1[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=1)=[O:30])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 86584855HCID 86584855, compoundHCID 178418676HCID 178418676, compound

Product 1

HCID 69428524HCID 69428524, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 200 mg (0.456 mmol) (2R,4R)-4-(4-Methoxy-benzylsulfanyl)-2-[2-(methoxy-methyl-carbamoyl)-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester in 3 ml THF was treated at 0° C. with 1.14 ml (1.14 mmol, 1M THF solution) of a 4-fluorophenyl-magnesium bromide solution and after 10 min warmed up to room temperature. The reaction was partitioned between aqueous aqueous 10% KHSO4/t-butyl methyl ether (3×). The organic phases were washed with aqueous 10% NaHCO3 and saturated NaCl solution, dried over MgSO4 and evaporated to give 144 mg (68%) of (2R,4R)-2-[3-(4-fluoro-phenyl)-3-oxo-propyl]-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 474 (MH+).

Workup

  1. customThe reaction was partitioned between aqueous aqueous 10% KHSO4/t-butyl methyl ether (3×)
  2. washThe organic phases were washed with aqueous 10% NaHCO3 and saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-4b461734d47144b9b5468751f3060d69
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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