Ammonia → HCID 25417766, compound

HRID 1671678Notes

Reaction equation

HRID 1671678 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:11]([C:12]([OH:14])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].OS(O)(=O)=O.[NH3:20]>CO>[C:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C@H:11]1[C:12](=[O:14])[NH2:20])=[O:7])([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 2734495(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid

Product 1

HCID 25417766HCID 25417766, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A mixture of 1-Boc-L-azetidine-2-carboxylic acid (10 g), conc. H2SO4 (1 mL) in dry MeOH (200 mL) was stirred at RT for 2 h. The reaction mixture was then concentrated in vacuo, the residue was diluted with EA, basified with sat. NaHCO3 solution. The organic extract was washed with water, dried (MgSO4), filtered and concentrated to yield the crude methyl ester as a yellow oil (11 g, 102%). This crude ester was dissolved in dry MeOH (200 mL) and treated with 7M ammonia solution in MeOH (100 mL). The resulting white suspension was stirred at RT for 72 h and filtered off. The filtrate was concentrated in vacuo to give the title compound as a white solid (8.5 g, 92%).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionthe residue was diluted with EA
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield the crude methyl ester as a yellow oil (11 g, 102%)
  9. stirringThe resulting white suspension was stirred at RT for 72 h
  10. filtrationfiltered off
  11. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9c3f4f7a5b8b4208853b4e9f5f5831e8
Source dataset
uspto-grants-2011_08
Patent number
US07994336B2

Reaction notes

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