Hydrogen Bromide → methyl (S)-1-((S)-2-(2-bromoacetyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

HRID 1471021Notes

Reaction equation

HRID 1471021 reaction equation
[N+](=[CH:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:21])[C@@H:12]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH:13]([CH3:15])[CH3:14])=[O:5])=[N-].[BrH:22]>CC(O)=O>[Br:22][CH2:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:21])[C@@H:12]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH:13]([CH3:15])[CH3:14])=[O:5]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 131731308Methyl (s)-1-((s)-2-(2-diazoacetyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate

Product 1

HCID 131732734methyl (S)-1-((S)-2-(2-bromoacetyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamateYield 76.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of Example 173D (70 mg, 0.236 mmol) in HOAc (0.6 mL) at ambient temperature was added 48% HBr (80 μL, 0.709 mmol). Mixture was stirred at ambient temperature for 1 hour. Mixture was poured into ice/H2O and extracted with CH2Cl2 (3×75 mL). Organic was dried (Na2SO4), filtered and concentrated afford 63 mg (76%) of the title compound. MS (ESI) m/z 350 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (3×75 mL)
  2. dry with materialOrganic was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b28b3428addd48e28e78278604c52be5
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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