Sodium Carbonate → HCID 90079938, compound

HRID 595039Notes

Reaction equation

HRID 595039 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([OH:14])=[O:13])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].S(Cl)(O[CH2:25][Cl:26])(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[C:1]([O:5][C:6]([NH:8][C:9]1([C:12]([O:14][CH2:25][Cl:26])=[O:13])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 90079938HCID 90079938, compound

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1-((tert-butoxycarbonyl)amino)cyclopropane-carboxylic acid (0.55 g, 2.73 mmol), sodium carbonate (1.449 g, 13.67 mmol) and tetrabutylammonium hydrogen sulfate (0.186 g, 0.547 mmol) in a mixture of DCM (10 mL) and water (5 mL) at 0° C., was added chloromethyl chlorosulfate (0.902 g, 5.47 mmol). The reaction mixture was allowed to warm to room temperature overnight. The mixture was diluted with DCM and water and the organic layer was separated, washed with a brine solution and dried over Na2SO4. The mixture was filtered and concentrated in vacuo and the residue obtained was purified by a flash chromatography (SiO2, 0-10% EtOAc in hexane) to afford Preparation 53A (0.5 g, 73.3%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 1.24-1.26 (m, 2H), 1.46 (s, 9H), 1.60-1.61 (m, 2H), 5.13 (s, 1H), 5.71 (s, 2H).

Workup

  1. customthe organic layer was separated
  2. washwashed with a brine solution
  3. dry with materialdried over Na2SO4
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated in vacuo
  6. customthe residue obtained
  7. customwas purified by a flash chromatography (SiO2, 0-10% EtOAc in hexane)
  8. customto afford

Sources & evidence

ORD record
ord-d7b7cde962414487a7fe1a21c9a670dd
Source dataset
uspto-grants-2016_01
Patent number
US09242941B2

Reaction notes

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