Lithium hydroxide, monohydrate → 3-tert-Butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid

HRID 624984Notes

Reaction equation

HRID 624984 reaction equation
[O:1]=[S:2]1(=[O:18])[CH2:6][CH:5]([C:7]([O:9]C)=[O:8])[N:4]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3]1.O.[OH-].[Li+]>C1COCC1.O>[C:14]([O:13][C:11]([N:4]1[CH:5]([C:7]([OH:9])=[O:8])[CH2:6][S:2](=[O:1])(=[O:18])[CH2:3]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 902041993-tert-Butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid methyl ester

Product 1

HCID 235209253-tert-Butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acidYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of O3-tert-butyl O4-methyl 1,1-dioxo-1,3-thiazolidine-3,4-dicarboxylate (Example 127 a, 0.35 g, 1.25 mmol) and lithium hydroxide hydrate (63.1 mg, 1.5 mmol) in THF (3.5 mL) and water (1.05 mL) was stirred for 20 h at ambient temperature. The reaction mixture was poured onto ice/0.1N HCl (25 mL) and extracted with EtOAc (2×25 mL). The combined extracts were washed with ice/brine (1×25 mL), dried over Na2SO4 and filtered. The solvent was removed under reduced pressure to give the title compound (306 mg, 92%) as colorless foam, MS (ESI) m/e=264.05 [M−H−].

Workup

  1. additionThe reaction mixture was poured onto ice/0.1N HCl (25 mL)
  2. extractionextracted with EtOAc (2×25 mL)
  3. washThe combined extracts were washed with ice/brine (1×25 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-22ff291b40104829acf072321f373cab
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

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