Lithium hydroxide, monohydrate → (5R)-1-(chloroacetyl)-5-ethynyl-L-proline

HRID 475348Notes

Reaction equation

HRID 475348 reaction equation
[Cl:1][CH2:2][C:3]([N:5]1[C@@H:13]([C:14]#[C:15][Si](C)(C)C)[CH2:12][CH2:11][C@H:6]1[C:7]([O:9]C)=[O:8])=[O:4].O[Li].O>CO.O>[Cl:1][CH2:2][C:3]([N:5]1[C@@H:13]([C:14]#[CH:15])[CH2:12][CH2:11][C@H:6]1[C:7]([OH:9])=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59683665methyl (5R)-1-(chloroacetyl)-5-((trimethylsilyl)ethynyl)-L-prolinate

Product 1

HCID 59683657(5R)-1-(chloroacetyl)-5-ethynyl-L-proline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of methyl (5R)-1-(chloroacetyl)-5-((trimethylsilyl)ethynyl)-L-prolinate (3.69 g, 12.2 mmol) in MeOH (24 mL) and H2O (24 mL) at room temperature was added LiOH•H2O (0.8 g, 18 mmol). The reaction mixture was stirred at ambient temperature overnight and concentrated under reduced pressure. The residue was taken up in water and extracted with diethyl ether (2×). The aqueous layer was acidified to pH˜3 by adding 4% KHSO4 dropwise. The solution was extracted with ethyl acetate (3×). Combined ethyl acetate layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to provide the titled compound. MS (CI) m/z 216 (M+1)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with diethyl ether (2×)
  3. additionby adding 4% KHSO4 dropwise
  4. extractionThe solution was extracted with ethyl acetate (3×)
  5. washCombined ethyl acetate layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a490cbbbb20943bd84ac2b815aa2a77c
Source dataset
uspto-grants-2014_01
Patent number
US08637546B2

Reaction notes

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