Hydrochloric Acid → HCID 77213633, compound

HRID 1361326Notes

Reaction equation

HRID 1361326 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]([CH:22]2[CH2:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23]2)[C:14](=[O:21])[C:15]([CH3:20])([CH3:19])[C:16](=[O:18])[CH3:17])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:30][Mg]Br.Cl>C1COCC1>[C:1]([N:8]1[CH2:12][CH2:11][CH:10]([N:13]([CH:22]2[CH2:27][CH2:26][C:25]([CH3:29])([CH3:28])[CH2:24][CH2:23]2)[C:14](=[O:21])[C:15]([CH3:19])([CH3:20])[C:16]([OH:18])([CH3:30])[CH3:17])[CH2:9]1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86636648HCID 86636648, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 77213633HCID 77213633, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S)-1-Boc-3-[(4,4-dimethylcyclohexyl)(2,2-dimethyl-3-oxobutanoyl)amino]pyrrolidine (100 mg, 0.25 mmol) prepared in Step A of Example C5 in THF was slowly added dropwise methylmagnesium bromide (in diethylether, 3.0M, 0.1 ml, 0.3 mmol) at 0° C., and the solution was stirred at rt for 2 h. After the reaction finished, to the solution was added 1N-HCl at 0° C., and extracted with EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent: EtOAc/Hex=1/3) to give the title compound (97 mg, 92%).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. custompurified by column chromatography (eluent: EtOAc/Hex=1/3)

Sources & evidence

ORD record
ord-99d4bc83d932452a86348bc77a7ae2e0
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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