2-N-Boc-aminopropionic acid → HCID 72978647, compound

HRID 1804686Notes

Reaction equation

HRID 1804686 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].S(Cl)(O[CH2:23][Cl:24])(=O)=O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.ClCCl.C(OCC)(=O)C>[Cl:24][CH2:23][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH3:13]

Participants

8

Reactant 3

HCID 2684712-N-Boc-aminopropionic acidHCID 516892Sodium BicarbonateHCID 2733556Chloromethyl chlorosulfate

Product 1

HCID 72978647HCID 72978647, compoundYield 97%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-tert-butoxycarbonylamino-propionic acid (0.507 g, 2.68 mol), sodium bicarbonate (1.13 g, 13.4 mmol) and tetrabutylammonium hydrogen sulfate (0.090 g, 0.268 mmol) in H2O (21 mL) at 0° C. was added dichloromethane (12 mL) and the mixture was stirred vigorously. Chloromethyl chlorosulfate (0.326 mL, 3.22 mmol) in dichloromethane (7 mL) was added and the mixture was warmed to rt overnight. The reaction mixture was diluted with ethyl acetate, washed with brine, dried (MgSO4) and concentrated. The resulting oil was purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane) to give a colorless oil (4) (0.6207 g, 97%). 1H NMR (300 MHz, CDCl3): 5.75 (d, J=5.4 Hz, 1H), 5.57 (d, J=5.4 Hz, 1H), 5.04 (br s, 1H), 4.28 (m, 1H), 1.37 (s, 9H), 1.32 (s, 3H).

Workup

  1. washwashed with brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe resulting oil was purified by flash column chromatography (silica gel, 0 to 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-453dc1d33c844905bb52bc3783411f8a
Source dataset
uspto-grants-2013_01
Patent number
US08354421B2

Reaction notes

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