methoxymethyl (4R)-3-benzoyl-1,1-dioxothiazolidine-4-carboxylate → (4R)-3-Benzoyl-1,1-dioxothiazolidine-4-carboxylic acid

HRID 1200144Notes

Reaction equation

HRID 1200144 reaction equation
[C:1]([N:9]1[C@H:13]([C:14]([O:16]COC)=[O:15])[CH2:12][S:11](=[O:21])(=[O:20])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.O>[C:1]([N:9]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][S:11](=[O:20])(=[O:21])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 13986806methoxymethyl (4R)-3-benzoyl-1,1-dioxothiazolidine-4-carboxylate

Product 1

HCID 13986804(4R)-3-Benzoyl-1,1-dioxothiazolidine-4-carboxylic acidYield 80.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

31.3 g of methoxymethyl (4R)-3-benzoyl-1,1-dioxothiazolidine-4-carboxylate (prepared as described in Preparation 11) were dissolved in 200 ml of a 1:1 by volume mixture of trifluoroacetic acid and water, and then the mixture was stirred at room temperature for 1 hour. The reaction mixture was then concentrated by evaporation under reduced pressure to leave crystals. These crystals were washed with 150 ml of water and then recrystallized from ethyl acetate to give 21.6 g (80.3%) of the title compound in the form of colorless needles melting at 175°-176° C.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. customto leave crystals
  3. washThese crystals were washed with 150 ml of water
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-559435ee05324a07adffa8734ea68131
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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